HCID 67016379, compound → HCID 67016370, compound

HRID 1919039Notes

Reaction equation

[CH3:1][C:2]1([CH3:43])[CH2:42][C:5]2[C:6]3[CH2:11][CH2:10][NH:9][CH:8]([C:12]4[C:13]([CH2:39][OH:40])=[C:14]([C:19]5[CH:20]=[C:21]([NH:27][C:28]6[CH:37]=[CH:36][C:35]7[CH2:34][N:33]([CH3:38])[CH2:32][CH2:31][C:30]=7[N:29]=6)[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=5)[CH:15]=[C:16]([F:18])[CH:17]=4)[C:7]=3[S:41][C:4]=2[CH2:3]1.Br[C:45]1C=C(NC2C=CC3CN(CC)CCC=3N=2)C(=O)N(C)C=1>>[CH3:1][C:2]1([CH3:43])[CH2:42][C:5]2[C:6]3[CH2:11][CH2:10][NH:9][CH:8]([C:12]4[C:13]([CH2:39][OH:40])=[C:14]([C:19]5[CH:20]=[C:21]([NH:27][C:28]6[CH:37]=[CH:36][C:35]7[CH2:34][N:33]([CH2:38][CH3:45])[CH2:32][CH2:31][C:30]=7[N:29]=6)[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=5)[CH:15]=[C:16]([F:18])[CH:17]=4)[C:7]=3[S:41][C:4]=2[CH2:3]1

Participants

Reactant 2

HCID 67016379HCID 67016379, compound

HCID 67016494HCID 67016494, compound

Product 1

HCID 67016370HCID 67016370, compoundYield 28%

Procedure

Using the same general procedure as described for the preparation of 240, reaction of 5-bromo-3-(6-ethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-ylamino)-1-methylpyridin-2(1H)-one (143 mg, 0.394 mmol) with 182c (300 mg, 0.513 mmol) gave a 28% yield (70 mg) of 241 as a yellow solid: mp 134-135° C.; 1H NMR (500 MHz, DMSO-d6) d 8.78 (d, 1H, J=2.0 Hz), 8.43 (s, 1H), 7.44 (d, 1H, J=2.0 Hz), 7.31 (dd, 1H, J=9.5, 2.5 Hz), 7.28 (d, 1H, J=8.0 Hz), 7.18 (dd, 1H, J=9.5, 2.5 Hz), 7.06 (d, 1H, J=8.0 Hz), 4.86 (m, 1H), 4.38 (m, 2H), 4.04 (m, 1H), 3.84 (m, 1H), 3.59 (s, 3H), 3.43 (s, 2H), 3.03 (m, 1H), 2.89 (m, 1H), 2.75 (s, 4H), 2.62 (m, 2H), 2.53 (m, 2H), 2.50 (m, 2H), 1.23 (s, 6H), 1.08 (t, 3H, J=7.0 Hz); MS (ESI+) m/z 628 (M+H).

Sources & evidence

ORD record: ord-8d0b710338394e3bb45381518fbe491f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618107B2

Reaction notes

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