Formic Acid → HCID 71247905, compound

HRID 1055147Notes

Reaction equation

HRID 1055147 reaction equation
[F:1][C:2]1[C:3]([NH:18][CH:19]([C:24]2([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][C:21]([OH:23])=[O:22])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.[CH:31](O)=O.[C:34](#N)[CH3:35]>>[C:24]12([CH:19]([NH:18][C:3]3[C:2]([F:1])=[CH:7][N:6]=[C:5]([C:8]4[C:16]5[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=5)[NH:10][CH:9]=4)[N:4]=3)[CH2:20][C:21]([OH:23])=[O:22])[CH2:30][CH:34]3[CH2:35][CH:28]([CH2:27][CH:26]([CH2:31]3)[CH2:25]1)[CH2:29]2

Participants

4

Reactant 3

HCID 284Formic AcidHCID 6342AcetonitrileHCID 71511508HCID 71511508, compound

Product 1

HCID 71247905HCID 71247905, compound

Procedure

Compound 86 was synthesized in a manner similar to 3-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)-3-(1-methylcyclohexyl)propanoic acid, 78, using adamantine-1-carbaldehyde as the starting material: 1H NMR (400 MHz, CD3OD) δ 8.75 (dd, J=9.7, 2.7 Hz, 1H), 8.18 (s, 2H), 8.00 (d, J=4.2 Hz, 1H), 2.81 (dd, J=15.2, 3.1 Hz, 1H), 2.55 (dd, J=15.2, 10.8 Hz, 1H), 2.00 (m, 3H), 1.82-1.49 (m, 12H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.40 minutes (M+H) 454.34.

Sources & evidence

ORD record
ord-dc3b43d6f5114fd2a736dbdbf894a803
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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