Acetic Acid → HCID 90412173, compound

HRID 1521971Notes

Reaction equation

HRID 1521971 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:16][C:9]=12.[C:32](O)(=[O:34])[CH3:33].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([C:32](=[O:34])[CH3:33])[CH2:30][CH2:31]2)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:16][C:9]=12

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90411712HCID 90411712, compound

Product 1

HCID 90412173HCID 90412173, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of Example 165 (20 mg, 0.05 mmol) in N,N-dimethylformamide (1 mL) was added acetic acid (4 mg, 0.07 mmol) and triethylamine (0.1 mL) at room temperature. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (11 mg, 0.07 mmol) and N-hydroxybenzotriazole (10 mg, 0.07 mmol) were added and the mixture was stirred overnight. Purification by HPLC (Zorbax XDB C-18 (32) using a gradient of 5-40% acetonitrile/water (containing 0.1% trifluoroacetic acid) afforded the title compound. 1H NMR (400 MHz, DMSO-d6): δ 1.57-1.93 (m, 5H), 1.96 (s, 3H), 2.28 (d, J=13.73 Hz, 2H), 2.80 (d, J=3.97 Hz, 3H), 2.87-3.01 (m, 2H), 3.02-3.22 (m, 5H), 3.52 (d, J=11.60 Hz, 2H), 3.77 (d, J=13.12 Hz, 2H), 4.34 (d, J=12.82 Hz, 2H), 6.10 (s, 1H), 6.61 (d, J=9.16 Hz, 1H), 7.11-7.18 (m, 1H), 7.56 (d, J=9.16 Hz, 1H), 8.23 (d, J=5.19 Hz, 1H). LCMS: 481 (M+H)+.

Workup

  1. customPurification by HPLC (Zorbax XDB C-18 (32)

Sources & evidence

ORD record
ord-138e90f9aabe49e79a912d1a89c822d4
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…