Cyclopentyl Isocyanate → 4-[2-Methyl-4-(6-morpholin-4-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-piperidine-1-carboxylic acid cyclopentylamide

HRID 731913Notes

Reaction equation

HRID 731913 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:17]3[CH:25]=[C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:23]=[CH:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH:32]1([N:37]=[C:38]=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33]1.FC1C=CC=C(F)C=1NC(N1CCC(OC2C=CC(NC3C4C=C(F)N=CC=4N=CN=3)=CC=2C)CC1)=O>>[CH:32]1([NH:37][C:38]([N:12]2[CH2:13][CH2:14][CH:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([NH:15][C:16]4[C:17]5[CH:25]=[C:24]([N:26]6[CH2:31][CH2:30][O:29][CH2:28][CH2:27]6)[N:23]=[CH:22][C:18]=5[N:19]=[CH:20][N:21]=4)=[CH:3][C:2]=3[CH3:1])[CH2:10][CH2:11]2)=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 643500Cyclopentyl IsocyanateHCID 69057517[3-Methyl-4-(piperidin-4-yloxy)-phenyl]-(6-morpholin-4-yl-pyrido[3,4-d]pyrimidin-4-yl)-amineHCID 865952374-[4-(6-Fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidine-1-carboxylic acid (2,6-difluoro-phenyl)-amide

Product 1

HCID 690576724-[2-Methyl-4-(6-morpholin-4-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-piperidine-1-carboxylic acid cyclopentylamide

Procedure

The title compound was prepared from [3-Methyl-4-(piperidin-4-yloxy)-phenyl]-(6-morpholin-4-yl-pyrido[3,4-d]pyrimidin-4-yl)-amine and cyclopentyl isocyanate by a procedure analogous to the synthesis of 4-[4-(6-Fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidine-1-carboxylic acid (2,6-difluoro-phenyl)-amide above. LRMS: 532.3/421.3 (MH+); 1H NMR (DMSO-d6, 400 MHz): δ 9.57 (s, 1H), δ 8.78 (s, 1H), δ 8.32 (s, 1H), δ 7.48-7.54 (m, 3H), δ 7.12 (d, J=9.14 1H), δ 6.24 (d, J=7.30, 1H), δ 4.50-5.19 (m, 1H), δ 3.84-3.89 (m, 1H), δ 3.74-3.76 (m, 4H), δ 3.51-3.59 (m, 6H), δ 3.12-3.18 (m, 2H), δ 2.16 (s, 3H), δ 1.81-1.86 (m, 4H), δ 1.29-1.76 (m, 8H).

Sources & evidence

ORD record
ord-b0a9857761174ab694b00a7c940e789b
Source dataset
uspto-grants-2009_09
Patent number
US07585869B2

Reaction notes

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