Pyrrolidine → HCID 11340957, compound

HRID 731915Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[C:22]4[CH:30]=[C:29](F)[N:28]=[CH:27][C:23]=4[N:24]=[CH:25][N:26]=3)=[CH:16][C:15]=2[CH3:32])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.C1(C(N2CCC(OC3C=CC(NC4C5C=C(N6CCCC6)N=CC=5N=CN=4)=CC=3C)CC2)=O)CCCC1>>[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[C:22]4[CH:30]=[C:29]([N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[N:28]=[CH:27][C:23]=4[N:24]=[CH:25][N:26]=3)=[CH:16][C:15]=2[CH3:32])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 31268Pyrrolidine

HCID 11202845Cyclopentyl-{4-[2-methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-piperidin-1-yl}-methanone

HCID 69054647HCID 69054647, compound

Product 1

HCID 11340957HCID 11340957, compound

Procedure

The Title compound was prepared from 3-[4-(6-Fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-benzoic acid tert-butyl ester and pyrrolidine by a procedure analogous to that described for the synthesis of Cyclopentyl-{4-[2-methyl-4-(6-pyrrolidin-1-yl-pyrido[3,4-d]pyrimidin-4-ylamino)-phenoxy]-piperidin-1-yl}-methanone. LRMS: 498.3 (MH+). 1H NMR (DMSO-d6, 400 MHz): δ 9.60 (s, 1H), δ 8.76 (s, 1H), δ 8.31 (s, 1H), δ 7.73-7.76 (m, 2H), δ 7.56-7.58 (m, 1H), δ 7.45 (t, J=7.89, 1H), δ 7.31-7.32 (m, 1H), δ 7.13-7.16 (m, 1H), δ 7.09 (s, 1H), 7.01 (d, J=9.14, 1H), δ 3.45-3.48 (m, 4H), δ 2.15 (s, 3H), δ 1.97-2.01 (m, 4H), δ 1.48 (s, 9H).

Sources & evidence

ORD record: ord-31939c0d5cbd4f8c91df7c3b26b937a1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585869B2

Reaction notes

Loading…