6-(3-Fluorophenyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzothiazole → HCID 178508363, compound

HRID 389580Notes

Reaction equation

HRID 389580 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[N:24][C:23]([NH2:26])=[C:22]4[O:27][C:28](Cl)=[CH:29][C:21]=34)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F:31][C:32]1[CH:33]=[C:34]([C:38]2[CH:46]=[CH:45][C:41]3[CH:42]=[N:43][S:44][C:40]=3[C:39]=2B2OC(C)(C)C(C)(C)O2)[CH:35]=[CH:36][CH:37]=1>>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:18]2[CH:17]=[N:16][N:15]([C@H:12]3[CH2:13][CH2:14][C@H:9]([OH:8])[CH2:10][CH2:11]3)[CH:19]=2)=[C:21]2[CH:29]=[C:28]([C:39]3[C:40]4[S:44][N:43]=[CH:42][C:41]=4[CH:45]=[CH:46][C:38]=3[C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([F:31])[CH:33]=3)[O:27][C:22]=12

Participants

3

Reactant 2

HCID 667607456-(3-Fluorophenyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzothiazoleHCID 178455334HCID 178455334, compound

Product 1

HCID 178508363HCID 178508363, compound

Procedure

The title compound was prepared from 4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-chlorofuro[2,3-c]pyridin-7-amine and 6-(3-fluorophenyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzothiazole by a procedure analogous to Example 229. 1H NMR (400 MHz, DMSO-d6): δ 9.21 (s, 1H), 8.55 (d, J=7.58 Hz, 1H), 8.28 (s, 1H), 8.07 (s, 1H), 7.98 (s, 1H), 7.97 (s, 1H), 7.79 (d, J=7.83 Hz, 1H), 7.59-7.72 (m, 3H), 7.34-7.43 (m, 1H), 6.34 (br s, 2H), 4.70 (d, J=4.29 Hz, 1H), 4.21 (tt, J=3.98, 11.56 Hz, 1H), 3.49-3.60 (m, 1H), 2.09 (br d, J=12.40 Hz, 2H), 1.83-2.02 (m, 4H), 1.33-1.46 (m, 2H); MS (ESI): 526.08 [M+H]+; HPLC tR=2.37 min (ZQ3: nonpolar—4 min).

Workup

  1. customHPLC tR=2.37 min (ZQ3: nonpolar—4 min)

Sources & evidence

ORD record
ord-a7963d5f0b3b45fca053c03a738c979e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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