Ethanolamine → HCID 57634219, compound

HRID 2109753Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=1)[CH2:10][N:11](C(OC(C)(C)C)=O)[C:12]1[S:13][C:14]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)=[C:15]([C:17]([O:19]C)=O)[N:16]=1)=O)(C)(C)C.[NH2:49][CH2:50][CH2:51][OH:52].C(O)(C(F)(F)F)=O>>[NH2:8][C@@H:9]([CH2:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]([F:47])([F:46])[F:48])=[CH:43][CH:44]=1)[CH2:10][NH:11][C:12]1[S:13][C:14]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)=[C:15]([C:17]([NH:49][CH2:50][CH2:51][OH:52])=[O:19])[N:16]=1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 6422Trifluoroacetic acid

HCID 57634039HCID 57634039, compound

Product 1

HCID 57634219HCID 57634219, compound

Procedure

The title compound was synthesized by treating the intermediate methyl 2-(((S)-2-(tert-butoxycarbonylamino)-3-(4-(trifluoromethyl)phenyl)propyl)(tert-butoxycarbonyl)amino)-5-(isoquinolin-6-yl)thiazole-4-carboxylate with 2-aminoethanol followed with a TFA treatment to remove the tert-butoxycarbonyl protecting groups. LCMS (M+H) calc. for C25H25F3N5O2S 516.2. 1H NMR (400 MHz, CD3OD) δ ppm 9.70 (s, 1H) 8.53-8.60 (m, 1H) 8.38-8.46 (m, 2H) 8.36 (s, 1H) 8.10-8.19 (m, 1H) 7.73 (d, J=6.85 Hz, 2H) 7.58 (d, J=6.85 Hz, 2H) 4.52-4.61 (m, 1H) 3.93 (s, 1H) 3.78-3.87 (m, 1H) 3.71 (t, J=5.48 Hz, 2H) 3.63 (dd, J=14.67, 6.46 Hz, 1H) 3.44-3.51 (m, 2H) 3.06-3.23 (m, 2H).

Workup

customto remove the tert-butoxycarbonyl protecting groups

Sources & evidence

ORD record: ord-422aa572ed03455f8290b0360ce5a51a
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514566B2

Reaction notes

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