1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178481812, compound

HRID 1096890Notes

Reaction equation

HRID 1096890 reaction equation
Cl.[CH3:2][N:3]1[C:7]([NH:8][C:9]2[CH:10]=[C:11]3[C:21](=[CH:22][CH:23]=2)[O:20][C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:13][C:12]3=[O:24])=[CH:6][CH:5]=[N:4]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[N:48]1([C:53]2[CH:54]=[C:55]([CH:59]=[C:60]([C:62]3[NH:66][N:65]=[N:64][N:63]=3)[CH:61]=2)[C:56](O)=[O:57])[CH2:52][CH2:51][CH2:50][CH2:49]1>O.CN(C=O)C.C(N(CC)CC)C>[CH3:2][N:3]1[C:7]([NH:8][C:9]2[CH:10]=[C:11]3[C:21](=[CH:22][CH:23]=2)[O:20][C:14]2([CH2:15][CH2:16][N:17]([C:56]([C:55]4[CH:59]=[C:60]([C:62]5[NH:63][N:64]=[N:65][N:66]=5)[CH:61]=[C:53]([N:48]5[CH2:52][CH2:51][CH2:50][CH2:49]5)[CH:54]=4)=[O:57])[CH2:18][CH2:19]2)[CH2:13][C:12]3=[O:24])=[CH:6][CH:5]=[N:4]1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 666494456-[(1-Methyl-1H-pyrazol-5-yl)amino]spiro[chroman-2,4'-piperidin]-4-one hydrochlorideHCID 178524188HCID 178524188, compound

Product 1

HCID 178481812HCID 178481812, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

6-[(1-Methyl-1H-pyrazol-5-yl)amino]spiro[chroman-2,4′-piperidin]-4-one hydrochloride (46 mg), 1-hydroxybenzotriazole monohydrate (17 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27 mg), triethylamine (34 μL) and water (660 μL) were added in that order to a DMF (2 mL) solution of 3-(pyrrolidin-1-yl)-5-(tetrazol-5-yl)benzoic acid (27 mg), and stirred at 90° C. for 2 hours and 30 minutes. Water was added to the reaction liquid, and the formed precipitate was taken out through filtration, once dried, then washed with hexane/ethyl acetate=3/2, and taken out through filtration. After dried, the title compound was obtained as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ: 7.92 (1.0H, s), 7.32 (1.0H, d, J=2.0 Hz), 7.21 (2.0H, s), 7.18-7.13 (2.0H, m), 6.99 (1.0H, d, J=9.2 Hz), 6.67 (1.0H, s), 5.89 (1.0H, s), 4.30-4.22 (1.0H, m), 3.61 (3.0H, s), 3.65-3.20 (3.0H, m), 2.81 (2.0H, s), 2.05-1.85 (9.0H, m), 1.85-1.70 (3.0H, m). MS [M+H]+=554.

Workup

  1. filtrationthe formed precipitate was taken out through filtration
  2. customonce dried
  3. washwashed with hexane/ethyl acetate=3/2
  4. filtrationtaken out through filtration
  5. customAfter dried

Sources & evidence

ORD record
ord-5d40e6a3f34844ee93cf5dfda512ab6a
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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