Trifluoroacetic acid → HCID 131734830, compound

HRID 1778551Notes

Reaction equation

HRID 1778551 reaction equation
C(OC([NH:8][C:9]1([CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:16][CH:15]2[N:17]([CH2:18][C:19]3[NH:24][C:23]([C:25]4[S:26][CH:27]=[CH:28][N:29]=4)=[N:22][C@@H:21]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=4[Cl:37])[C:20]=3[C:38]([O:40][CH3:41])=[O:39])[CH:11]([CH2:12][O:13][CH2:14]2)[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1([CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:10][CH:11]2[N:17]([CH2:18][C:19]3[NH:24][C:23]([C:25]4[S:26][CH:27]=[CH:28][N:29]=4)=[N:22][C@@H:21]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=4[Cl:37])[C:20]=3[C:38]([O:40][CH3:41])=[O:39])[CH:15]([CH2:14][O:13][CH2:12]2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117709962HCID 117709962, compound

Product 1

HCID 131734830HCID 131734830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 146b (0.14 g, 0.20 mmol), TFA (2 mL) in DCM (5 mL) was stirred for 2 hours. The solvents were removed under reduced pressure to give crude methyl (4R)-6-[[7-amino-7-(2-ethoxy-2-oxo-ethyl)-3-oxa-9-azabicyclo[3.3.1]nonan-9-yl]methyl]-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate in TFA salt form. MS: calc'd (MH +) 592, exp (MH+) 592. This TFA salt (35 mg, 0.051 mmol) was dissolved in a mixture of TEA (20.6 mg, 0.204 mmol) in DCM (3 mL). To it was added CH3SO2Cl (11.7 mg, 0.102 mmol). The resulting mixture was stirred for 12 hours at room temperature, and concentrated under reduced pressure. The residue was purified by preparative HPLC to give two products, Example 146 and Example 147.

Workup

  1. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-02502b8b50214d32969366c2d40e4c38
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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