5-Bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one → HCID 54596456, compound

HRID 1919021Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C([O:20][CH2:21][C:22]1[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=[CH:24][C:23]=1[N:37]1[CH2:49][CH2:48][C:47]2[N:46]3[C:41]([CH2:42][CH2:43][CH2:44][CH2:45]3)=[CH:40][C:39]=2[C:38]1=[O:50])(=O)C>>[OH:20][CH2:21][C:22]1[C:27]([C:2]2[CH:3]=[C:4]([NH:10][C:11]3[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)=[CH:26][CH:25]=[CH:24][C:23]=1[N:37]1[CH2:49][CH2:48][C:47]2[N:46]3[C:41]([CH2:42][CH2:43][CH2:44][CH2:45]3)=[CH:40][C:39]=2[C:38]1=[O:50]

Participants

Reactant 2

HCID 580441425-Bromo-1-methyl-3-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

HCID 67016985HCID 67016985, compound

Product 1

HCID 54596456HCID 54596456, compoundYield 17%

Procedure

Using the same general procedure as described for 118, reaction of 112a (200 mg, 0.706 mmol) and 118f (330 mg, 0.710 mmol) afforded a 17% yield (60 mg) of 225 as a green-yellow solid: mp 199-200° C.; 1H NMR (500 MHz, DMSO-d6) d 11.69 (s, 1H), 7.99 (s, 1H), 7.93 (s, 1H), 7.41 (t, 1H, J=8.0 Hz), 7.25 (d, 3H, J=8.5 Hz), 6.00 (s, 1H), 5.86 (s, 1H), 4.69 (br s, 1H), 4.31 (m, 2H), 3.97 (m, 1H), 3.91 (m, 1H), 3.79 (m, 2H), 3.56 (s, 3H), 3.01 (m, 1H), 2.90 (m, 1H), 2.70 (m, 2H), 2.15 (s, 3H), 1.90 (m, 2H), 1.74 (m, 2H); MS (ESI+) m/z 499.2 (M+H).

Sources & evidence

ORD record: ord-06f8d0cb1d4e4a86b6c72bddb514e514
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618107B2

Reaction notes

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