Trifluoroacetic acid → HCID 178434249, compound

HRID 598832Notes

Reaction equation

HRID 598832 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([NH:16][C:17](=O)[C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[N:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)(C(F)(F)F)=O>>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=1)[CH2:17][NH:16][C:14]1[O:15][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])=[CH:12][N:13]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226445Aluminium lithium hydrideHCID 178434254HCID 178434254, compound

Product 1

HCID 178434249HCID 178434249, compound

Procedure

The compound was synthesized by reducing tert-butyl(S)-1-(5-(3-methyl-1H-indazol-5-yl)oxazol-2-ylamino)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate with LAH followed with a TFA treatment. LCMS (API-ES) m/z (%): 416 (100%, M++H); 1H NMR (400 MHz, MeOH-d4) δ ppm 6.31 (s, 1H) 6.12 (d, J=8.02 Hz, 2H) 5.91-6.03 (m, 4H) 5.75 (s, 1H) 2.27 (dd, J=7.14, 4.40 Hz, 1H) 2.07-2.15 (m, 1H) 1.97-2.07 (m, 1H) 1.56-1.64 (m, 1H) 1.54 (d, J=6.85 Hz, 1H).

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-8addae7896fe4fd6aaf4066442ea3c7b
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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