Isopropylamine → HCID 21276962, compound

HRID 2292136Notes

Reaction equation

[CH3:1]N(C1C=CC=CN=1)C.[CH:10]1([N:16]=[C:17]=[N:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15]CCCC1.[C:25]([NH:29][C:30]([C:32]1[CH:33]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[Cl:62])[C:34]([C:53](O)=[O:54])=[C:35]([CH2:39][O:40]CCN2C3C=CC=CC=3N=C2C)[NH:36][C:37]=1[CH3:38])=[O:31])([CH3:28])([CH3:27])[CH3:26].[CH:63]([NH2:66])([CH3:65])[CH3:64]>ClCCl>[C:25]([NH:29][C:30]([C:32]1[CH:33]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[Cl:62])[C:34]([C:53](=[O:54])[NH:66][CH:63]([CH3:65])[CH3:64])=[C:35]([CH2:39][O:40][CH2:15][CH2:10][N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]2[CH3:1])[NH:36][C:37]=1[CH3:38])=[O:31])([CH3:26])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 24 °C

Procedure

Dimethylaminopyridine (0.026 g, 0.21 mmol) and N,N'-dicyclohexylcarbodiimide (0.048 g, 0.23 mmol) were added to a stirred suspension of 5-(N-t-butylcarbamoyl)-3-carboxy-4-(2-chlorophenyl)-6-methyl-2-[2-(2-methylbenzimidazol-1-yl)ethoxymethyl]-1,4-dihydropyridine (0.107 g, 0.2 mmol) in dry dichloromethane (2 ml). The mixture was stirred for 16 hours at 24° C. and then treated with isopropylamine (0.17 ml, 2 mmol). The mixture was stirred for a further 3 hours and the solvent then evaporated and the residue chromatographed on silica gel, eluting with a mixture of methanol and ethyl acetate (1:9) to afford the title compound as a colourless oil which crystallised on standing (0.08 g, 68%), m.p. 191-193° C. Found: C, 66.18; H, 7.38; N, 11.72. C32H40ClN5O3 requires: C, 66.48; H, 6.97; N, 12.11%.

Workup

stirringThe mixture was stirred for a further 3 hours
customthe solvent then evaporated
customthe residue chromatographed on silica gel
washeluting with a mixture of methanol and ethyl acetate (1:9)

Sources & evidence

ORD record: ord-798473c77979483b947c64afc5362477
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801598

Reaction notes

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