(S)-2-(Piperidin-2-yl)ethanamine → HCID 54713622, compound

HRID 1622951Notes

Reaction equation

HRID 1622951 reaction equation
N1CCCC[C@H]1CCN.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[CH2:18][NH:19][C:20]([C:22]1[C:23](=[O:49])[C:24]([O:41]CC2C=CC=CC=2)=[C:25]2[C:38](=[O:39])[N:29]3[CH2:30][CH2:31][C@@H:32]4[CH2:37][CH2:36][CH2:35][CH2:34][N:33]4[C@@H:28]3[CH2:27][N:26]2[CH:40]=1)=[O:21]>>[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[CH2:18][NH:19][C:20]([C:22]1[C:23](=[O:49])[C:24]([OH:41])=[C:25]2[C:38](=[O:39])[N:29]3[CH2:30][CH2:31][C@@H:32]4[CH2:37][CH2:36][CH2:35][CH2:34][N:33]4[C@@H:28]3[CH2:27][N:26]2[CH:40]=1)=[O:21]

Participants

3

Reactant 2

HCID 667728(S)-2-(Piperidin-2-yl)ethanamineHCID 66594467HCID 66594467, compound

Product 1

HCID 54713622HCID 54713622, compoundYield 107.3%

Procedure

In a manner similar to that described in example Z-35, from {2-[(2S)-2-piperidinyl]ethyl}amine (28 mg, 0.218 mmol) and 16a (30 mg, 0.0638 mmol) was prepared (4aS,14aS)—N-[(2,4-difluorophenyl)methyl]8,10-dioxo-9-[(phenylmethyl)oxy]-2,3,4,4a,5,6,8,10,14,14a-decahydro-1H-pyrido[1,2-c]pyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-11-carboxamide (29 mg, 82%). This material was deprotected in a second step similar to that described in example Z-37 to give the title compound as a white solid (26 mg, quantitative), 1H NMR (CDCl3) δ 12.44 (br s, 1H), 10.48 (s, 1H), 8.26 (s, 1H), 7.35 (m, 1H), 6.80 (m, 2H), 4.68-4.67 (m, 2H), 4.38 (m, 1H), 4.20 (m, 1H), 3.93 (s, 1H), 3.63-3.39 (m, 2H), 2.91 (m, 2H), 2.29 (br s, 1H), 2.02 (m, 1H), 1.69-1.45 (m, 4H), 1.30-1.24 (m, 2H), 1.12 (br s, 1H); ES+ MS: 459 (M+1).

Sources & evidence

ORD record
ord-33008c391e7d4f529dc73138befd9597
Source dataset
uspto-grants-2014_07
Patent number
US08778943B2

Reaction notes

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