Hydrochloric Acid → HCID 178508372, compound

HRID 389585Notes

Reaction equation

HRID 389585 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:40]=[CH:39][C:35]2[N:36]=[CH:37][S:38][C:34]=2[C:33]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=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[CH2:11][CH2:10][C@H:9]([OH:8])[CH2:14][CH2:13]3)[CH:19]=2)=[C:21]2[CH:29]=[C:28]([C:33]3[C:34]4[S:38][CH:37]=[N:36][C:35]=4[CH:39]=[CH:40][C:32]=3[F:31])[O:27][C:22]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66760403(6-Fluoro-1,3-benzothiazol-7-yl)boronic acidHCID 178455334HCID 178455334, compound

Product 1

HCID 178508372HCID 178508372, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-chlorofuro[2,3-c]pyridin-7-amine (70.5 mg, 0.158 mmol), (6-fluoro-1,3-benzothiazol-7-yl)boronic acid (44.0 mg, 0.22 mmol), and Pd(PPh3)4 (18.2 mg, 0.0158 mmol) in 1,4-dioxane (1.23 mL) and aqueous 1.0 N sodium carbonate solution (0.615 mL, 0.615 mmol) was heated to 120° C. in a microwave for 60 min. Into the reaction mixture was added hydrochloric acid in 1,4-dioxane (4 N in 1,4-dioxane, 0.59 mL, 2.36 mmol), and the reaction mixture was stirred at rt for 30 min, then purified by MDPS to afford 4.4 mg (6%) of the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 9.63 (s, 1H), 8.23 (s, 1H), 8.21 (s, 1H), 8.18 (s, 1H), 8.16 (s, 1H), 7.91 (s, 1H), 7.81 (s, 1H), 6.52 (brs, 2H), 4.67 (brd, J=3.2 Hz, 1H), 4.21 (tt, J=11.4, 4.0 Hz, 1H), 3.55-3.45 (m, 1H), 2.08-2.02 (m, 2H), 1.97-1.78 (m, 4H), 1.44-1.30 (m, 2H); MS (ESI): 450.03 [M+H]+; HPLC: tR=2.85 min (ZQ3: polar—5 min).

Workup

  1. custompurified by MDPS

Sources & evidence

ORD record
ord-0dcd7e7e0f6e46d2a70fcabf988226b6
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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