1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67416494, compound

HRID 1803597Notes

Reaction equation

HRID 1803597 reaction equation
Cl.[CH2:2]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([NH2:21])[C:9]([CH3:20])=[C:10]([NH:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:11]=1)[CH3:3].[Cl:22][C:23]1[C:32]2[C:27](=[CH:28][C:29]([C:33]([OH:35])=[O:34])=[CH:30][CH:31]=2)[C:26](=[O:36])[NH:25][N:24]=1.ClC1C2C(=CC=C(C(O)=O)C=2)C(=O)NN=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.CCN(CC)CC>[CH:33]([OH:35])=[O:34].[CH2:2]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[C:9]([CH3:20])=[C:8]([NH:21][C:33]([C:29]2[CH:28]=[C:27]3[C:32](=[CH:31][CH:30]=2)[C:23]([Cl:22])=[N:24][NH:25][C:26]3=[O:36])=[O:34])[CH:7]=1)[CH3:3]

Participants

8

Reactant 5

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67416453HCID 67416453, compoundHCID 67417448HCID 67417448, compoundHCID 67417752HCID 67417752, compound

Product 1

HCID 67416494HCID 67416494, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-ethoxymethyl-2-methyl-N-(2-pyrrolidin-1-yl-ethyl)-benzene-1,3-diamine hydrochloride (430 mg, 1.55 mmol), 1-chloro-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid (331 mg, 1.476 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (863 mg, 4.50 mmol), NEt3 (0.82 mL, 5.904), 1-hydroxybenzotriazole hydrate (259 mg, 1.919 mmol) and anhydrous DMF was stirred at room temperature for 2.5 h. The reaction mixture was filtered through celite, rinsed with CH2Cl2 and concentrated. Preparatory HPLC afforded 1-chloro-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid [5-ethoxymethyl-2-methyl-3-(2-pyrrolidin-1-yl-ethylamino)-phenyl]-amide formic acid salt (72 mg) as an orange solid. 1H NMR (400 MHz, d6-DMSO) δ: 1.15 (t, 3H), 1.72 (m, 4H), 1.93 (s, 3H), 2.58 (m, 4H), 2.74 (t, 2H), 3.22 (m, 2H), 3.46 (q, 2H), 4.38 (s, 2H), 4.93 (bs, 1H), 6.49 (s, 1H), 6.56 (s, 1H), 8.18 (s, 1H), 8.39 (d, 1H), 8.46 (d, 1H), 8.52 (s, 1H), 10.40 (s, 1H), 13.00 (s, 1H) ppm; m/z (M+1) 484.33; and 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid [5-ethoxymethyl-2-methyl-3-(2-pyrrolidin-1-yl-ethylamino)-phenyl]-amide formic acid salt (78 mg) as an orange solid. 1H NMR (400 MHz, d6-DMSO) δ: 1.14 (t, 3H), 1.73 (m, 4H), 1.93 (s, 3H), 2.61 (m, 4H), 2.77 (t, 2H), 3.24 (m, 2H), 3.47 (m, 2H), 4.37 (s, 2H), 4.95 (bs, 1H), 6.50 (s, 1H), 6.57 (s, 1H), 8.12 (d, 1H), 8.18 (s, 1H), 8.52 (d, 1H), 8.88 (s, 1H), 10.40 (s, 1H), 13.02 (s, 1H) ppm; m/z (M+1) 484.33.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washrinsed with CH2Cl2
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a4be963f72a24f0aa55eae0c88a5fb27
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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