Glycolic Acid → HCID 68690829, compound

HRID 1441339Notes

Reaction equation

HRID 1441339 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([C:20]4[N:24]([CH:25]([CH3:27])[CH3:26])[C:23]([CH3:28])=[N:22][CH:21]=4)[C:17]([F:29])=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:3]1.[C:30](O)(=[O:33])[CH2:31][OH:32]>>[F:29][C:17]1[C:18]([C:20]2[N:24]([CH:25]([CH3:26])[CH3:27])[C:23]([CH3:28])=[N:22][CH:21]=2)=[N:19][C:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([N:4]3[CH2:5][CH2:6][C@@H:2]([NH:1][C:31](=[O:32])[CH2:30][OH:33])[CH2:3]3)=[CH:12][CH:11]=2)=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 68687076HCID 68687076, compound

Product 1

HCID 68690829HCID 68690829, compound

Procedure

The title compounds was prepared (38 mg, 15%), was prepared using a procedure analogous to Example 155 starting from N-{4-[(3R)-3-aminopyrrolidin-1-yl]phenyl}-5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine (Example 156; 220 mg, 0.556 mmol) and glycolic acid (51 mg, 0.667 mmol). NMR: 1.39 (d, 6H), 1.92-2.04 (m, 1H), 2.14-2.26 (m, 1H), 2.44 (s, 3H), 3.04-3.13 (m, 1H), 3.18-3.49 (m, 3H), 3.80 (d, 2H), 4.46-4.51 (m, 1H), 5.34 (t, 1H), 5.42-5.51 (m, 1H), 6.49 (d, 2H), 7.31 (d, 1H), 7.35 (d, 2H), 7.82 (d, 1H), 8.41 (d, 1H), 9.06 (s, 1H); m/z 454.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-08c235b1d2e6491c802e7e19c99ed286
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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