Triethylamine → HCID 117706704, compound

HRID 1778490Notes

Reaction equation

HRID 1778490 reaction equation
[NH2:1][CH:2]1[CH2:9][C@@H:8]2[N:10]([CH2:11][C:12]3[NH:17][C:16]([C:18]4[S:19][CH:20]=[CH:21][N:22]=4)=[N:15][C@@H:14]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=4[Cl:30])[C:13]=3[C:31]([O:33][CH3:34])=[O:32])[C@@H:4]([CH2:5][O:6][CH2:7]2)[CH2:3]1.C(N(CC)CC)C.Cl[S:43]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=[O:45])=[O:44]>C(Cl)Cl>[C:49]([O:48][C:47]([NH:46][S:43]([NH:1][CH:2]1[CH2:3][C@@H:4]2[N:10]([CH2:11][C:12]3[NH:17][C:16]([C:18]4[S:19][CH:20]=[CH:21][N:22]=4)=[N:15][C@@H:14]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=4[Cl:30])[C:13]=3[C:31]([O:33][CH3:34])=[O:32])[C@@H:8]([CH2:7][O:6][CH2:5]2)[CH2:9]1)(=[O:45])=[O:44])=[O:53])([CH3:52])([CH3:50])[CH3:51]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 117706698HCID 117706698, compound

Product 1

HCID 117706704HCID 117706704, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl (4R)-6-[[(1S,5R)-7-amino-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 60b (60 mg, 0.12 mmol) and triethylamine (0.17 mL, 1.2 mmol) in DCM (5 mL) was added a 0.05 M solution of tert-butyl N-chlorosulfonylcarbamate in DCM (2.5 mL, 0.125 mmol) dropwise at 0° C. The mixture was allowed to warm to room temperature while stirred for 16 h, and then concentrated in vacuo. The residue was purified by silica gel chromatography to afford 0.08 g of methyl (4R)-6-[[(1S,5R)-7-(tert-butoxycarbonylsulfamoylamino)-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 63a as a yellow oil (yield was 97%). MS: calc'd (MH+) 684, measured (MH+) 684.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c4fae3432dce41708bb4727619af9a8f
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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