HCID 10659450, compound → HCID 5481926, compound

HRID 1419705Notes

Reaction equation

HRID 1419705 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([C:15]([OH:17])=O)=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1)#[N:2].[NH2:18][C@H:19]([CH3:36])[C@:20]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[F:35])([OH:27])[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]([C:15]([NH:18][C@H:19]([CH3:36])[C@:20]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[F:35])([OH:27])[CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)=[O:17])=[C:12]([CH3:14])[N:13]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 10659450HCID 10659450, compoundHCID 106817292-(4-Cyanophenyl)-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 5481926HCID 5481926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following a similar procedure to that described in example 1 but using 2-(4-cyanophenyl)-4-methylthiazole-5-carboxylic acid (reference example 24) and (2R,3R)-3-amino-2-(2,4-difluorophenyl)-1-(1H-imidazol-1 -yl)-2-butanol (75 mg, 0.28 mmol, obtained following the general procedure described in J. Org. Chem., 1995, 60, 3000-3012) in DMF (5 mL) the title compound was obtained as a white solid: mp 126°-128° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.05 (dt, Jt =2, Jd =8.4, 2H, arom), 7.50 (dt, Jt =2, Jd =8.4, 2H, arom), 7.47 (dt, Jd =6.5, Jt =8.8, 1H, arom), 7.24 (s, 1H, imidazole), 6.84.6 (m, 2H, arom), 6.52 (br d, J=9.5, 1H, NH, 6.51 (s, 1H, imidazole), 6.32 (s, 1H, imidazole), 4.85 (br quint, J=7, 1H, CHMe), 4.68 (d, J=14.5, 1H, ImCH(H)), 4.29 (d, J=14.5, 1H, ImCH(H)), 2.80 (s, 3H, Me-thiazole), 1.06 (d, J=6.8, 3H, MeCH); MS 227 (acyl group, C12H7N2OS), 223 (Im--CH2COHAr, C11H9F2N2O); [α]D =-20.4° (c 1, CHCl3). Analysis calculated for C25H21F2N5O2S: C 60.84; H 4.29; N 14.19; S 6.50 Found: C 60.85; H 4.31; N 13.75; S 6.18.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-bcbebaa73ece43288f4c4b2d4d8a9ee7
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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