Cyclopentylamine → HCID 59553369, compound

HRID 1171357Notes

Reaction equation

HRID 1171357 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([CH3:36])[CH2:32][CH2:31]2)[CH:29]=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](SC)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[CH:37]1([NH2:42])[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH:37]1([NH:42][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:27]=[C:28]([N:30]5[CH2:35][CH2:34][CH:33]([CH3:36])[CH2:32][CH2:31]5)[CH:29]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH:10]=3)[CH:24]=[CH:23][N:22]=2)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 59553063HCID 59553063, compound

Product 1

HCID 59553369HCID 59553369, compound

Procedure

Compound is prepared from 3-fluoro-5-(4-methylpiperidin-1-yl)-N-(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)benzamide (0.2 mmol) and cyclopentylamine (10 mmol) according to conditions described in Step 4 of Example 3 and general procedure C. A yellow solid (13 mg); Mp: 88-90° C.; 1H NMR (300 MHz, CDCl3) δ 0.98 (d, J=6.6 Hz, 3H), 1.23-1.87 (m, 13H), 2.77-2.85 (m, 2H), 3.76 (d, J=12.3 Hz, 2H), 4.08-4.15 (m, 1H), 5.15 (bs, 1H), 6.04 (s, 1H), 6.76 (d, J=12.3 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H), 7.26-7.30 (m, 2H), 7.49-7.55 (m, 2H), 7.87-7.97 (m, 3H), 8.07-8.11 (m, 1H), 8.20 (s, 1H); MS 540 (M+1).

Sources & evidence

ORD record
ord-135622591e5542939beee45bb52e36c2
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

Loading…