Cyclopentylamine → HCID 59553207, compound

HRID 1171273Notes

Reaction equation

HRID 1171273 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[CH:38]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH:38]1([NH:43][C:21]2[N:20]=[C:19]([O:18][C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:29]=[C:30]([N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)[CH:31]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH:10]=3)[CH:24]=[CH:23][N:22]=2)[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 595530953-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide

Product 1

HCID 59553207HCID 59553207, compound

Procedure

Compound is prepared from 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide (0.1 mmol) and cyclopentylamine (10 mmol) according to conditions described in general procedure C. Compound is produced (25 mg) as a light yellow solid; Mp: 119-120° C.; 1H NMR (300 MHz, CDCl3) δ 1.23-1.38 (m, 4H), 1.53-1.88 (m, 4H), 3.22-3.25 (m, 4H), 3.84-3.86 (m, 4H), 4.08-4.15 (m, 1H), 5.06 (bs, 1H), 6.07 (bs, 1H), 6.76 (d, J=11.7 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 7.25-7.31 (m, 2H), 7.48-7.58 (m, 2H), 7.85-7.98 (m, 3H), 8.14 (s, 1H), 8.25 (s, 1H); MS: 528 (M+1).

Workup

  1. customCompound is produced (25 mg) as a light yellow solid

Sources & evidence

ORD record
ord-a0a3a58a3f8d4719be809fc7edf659a4
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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