Isobutyric Acid → HCID 57721186, compound

HRID 1986382Notes

Reaction equation

HRID 1986382 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)[C:9]3[CH:14]=[C:13]([O:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:23]=2)=[N:4][O:5][N:6]=1.[CH3:31][CH:32]([CH3:36])[C:33](O)=[O:34].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:31][CH:32]([CH3:36])[C:33]([O:30][C:27]1[CH:28]=[CH:29][C:24]([N:8]2[C:9]3[CH:14]=[C:13]([O:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:23]=[C:7]2[C:3]2[C:2]([NH2:1])=[N:6][O:5][N:4]=2)=[CH:25][CH:26]=1)=[O:34]

Participants

7

Reactant 5

HCID 6590Isobutyric AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68873899HCID 68873899, compound

Product 1

HCID 57721186HCID 57721186, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product of Step 4 (80 mg, 0.20 mmol) and 2-methylpropanoic acid (18.4 mg, 0.21 mmol) in 2 ml DMF was treated with 1-hydroxybenzotriazole hydrate (HOBT)(29.7 mg, 0.22 mmol). The resulting mixture was stirred for 10 minutes at room temperature before being treated with triethylamine (22 mg, 0.22 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (42 mg, 0.22 mmol). The reaction was kept at room temperature overnight. Purification of the crude mixture by reverse phase (CH3CN 30%-80% in H2O with 0.1% TFA) afforded 20 mg (31%) oil as title compound. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.89 (s, 1H), 7.68 (d, 2H, 8.8 Hz), 7.38 (d, 2H, 8.8 Hz), 7.32 (t, 1H, 8.0 Hz), 6.85 (d, 1H, 7.6 Hz), 6.79-6.91 (m, 3H), 5.5-6.8 (M, 6H), 2.88 (m, 1H), 1.28 (d, 6H, 6.8 Hz). MS (ES+) m/e 372.2 [M+H]+.

Workup

  1. waitThe reaction was kept at room temperature overnight
  2. customPurification of the crude mixture by reverse phase (CH3CN 30%-80% in H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-c4ea1d5a09c94bd6897e3d802c58d7a2
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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