L-Alaninol → HCID 90313261, compound

HRID 1524013Notes

Reaction equation

HRID 1524013 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([C:20]([OH:22])=O)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:23])=[CH:4][N:3]=1.[NH2:24][C@@H:25]([CH3:28])[CH2:26][OH:27].FC(F)(F)[C@@H](N)C>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([C:20]([NH:24][C@@H:25]([CH3:28])[CH2:26][OH:27])=[O:22])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:23])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 80307L-AlaninolHCID 10964447(S)-1,1,1-trifluoropropan-2-amineHCID 90313349HCID 90313349, compound

Product 1

HCID 90313261HCID 90313261, compound

Procedure

The title compound was prepared using methods analogous to those described in Step C of Example 504 using 4′-(2-aminopyrazin-5-yl)-3′-fluoro-[1,1′-biphenyl]-2-carboxylic acid and (S)-2-aminopropan-1-ol for (S)-1,1,1-trifluoropropan-2-amine. MS (ESI): mass calcd. for C20H19FN4O2, 366.15; m/z found, 367.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1H), 8.05 (d, J=5.1, 2H), 7.93-7.83 (m, 1H), 7.54-7.43 (m, 3H), 7.37-7.28 (m, 2H), 6.72 (s, 2H), 4.66 (t, J=5.6, 1H), 3.82 (d, J=7.0, 1H), 3.35 (s, 1H), 3.16 (d, J=10.4, 2H), 0.98 (d, J=6.6, 3H).

Sources & evidence

ORD record
ord-f8e67727cd2f43fea54db314e4a94091
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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