Diisopropylethylamine → 4'-Fluoro-biphenyl-4-carboxylic acid [2-(isopropyl-methyl-amino)-benzothiazol-6-yl]-amide

HRID 1174912Notes

Reaction equation

HRID 1174912 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:41]([N:44]([CH3:55])[C:45]1[S:46][C:47]2[CH:53]=[C:52]([NH2:54])[CH:51]=[CH:50][C:48]=2[N:49]=1)([CH3:43])[CH3:42].CCN(C(C)C)C(C)C>C(Cl)Cl.CO>[CH:41]([N:44]([CH3:55])[C:45]1[S:46][C:47]2[CH:53]=[C:52]([NH:54][C:12]([C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:16][CH:15]=3)=[O:14])[CH:51]=[CH:50][C:48]=2[N:49]=1)([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27826894-(4-Fluorophenyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57771707N2-Isopropyl-N2-methyl-benzothiazole-2,6-diamine

Product 1

HCID 577717944'-Fluoro-biphenyl-4-carboxylic acid [2-(isopropyl-methyl-amino)-benzothiazol-6-yl]-amideYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Prepare according to Method A, using 4-(4-fluorophenyl)benzoic acid (253 mg, 1.17 mmol), HATU (451 mg, 1.19 mmol), N2-Isopropyl-N2-methyl-benzothiazole-2,6-diamine (200 mg, 0.904 mmol), DIEA (520 μL, 2.99 mmol), and a chromatography gradient of MeOH in CH2Cl2 (0-5%) to afford the title compound (196 mg, 52%). mass spectrum (m/e): 420.0 [M+H], 418.0 [M−H]. 1H NMR (400 MHz, DMSO-d6): δ 10.28 (s, 1H), 8.27 (d, 1H, J=2.2 Hz), 8.06 (d, 2H, J=8.4 Hz), 7.85-7.78 (m, 4H), 7.56 (dd, 1H, J=8.8, 2.2 Hz), 7.40 (d, 1H, J=8.2 Hz), 7.37-7.31 (m, 2H), 4.34 (m, 1H), 2.98 (s, 3H), 1.23 (d, 6H, J=6.6 Hz).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-b6a92deb3238405d8bd20b771905453a
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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