Propyl isocyanate → HCID 58677637, compound

HRID 1012618Notes

Reaction equation

HRID 1012618 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.[CH2:27]([N:30]=[C:31]=[O:32])[CH2:28][CH3:29]>N1C=CC=CC=1>[Cl:25][C:11]1[CH:12]=[C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH:14]=[CH:15][C:10]=1[C:8]([C:6]1[CH:7]=[C:2]([NH:1][C:31]([NH:30][CH2:27][CH2:28][CH3:29])=[O:32])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677637HCID 58677637, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in pyridine (0.2 mL) and n-propyl isocyanate (0.011 mL, 0.12 mmol) was added. The solution was stirred at room temperature for 18 h. Work up as described in, the preparation of compound 259. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 1:1 as the eluent. This afforded the title compound as a slightly coloured solid. 13C NMR (CD3OD) δ 198.5, 161.0 (dd), 158.3, 157.9 (dd), 151.1, 141.0, 138.9, 136.1, 135.0, 132.7, 132.1, 128.9, 127.4 (dd), 126.0 (dd), 122.5, 120.9, 116.6, 112.9, 112.6 (dd), 105.8 (dd), 42.6, 24.4, 19.7, 11.6

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f9939a78f6614be88492c19a16c18523
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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