Trimethylsilyl isocyanate → HCID 58189244, compound

HRID 1423191Notes

Reaction equation

HRID 1423191 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([CH3:28])=[N:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C[Si]([N:42]=[C:43]=[O:44])(C)C>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([CH3:28])=[N:19][N:20]3[CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)=[CH:16][CH:15]=2)[CH2:11][CH2:12][N:13]1[C:43]([NH2:42])=[O:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70696Trimethylsilyl isocyanate2×HCID 81531DiisopropylethylamineHCID 23627509HCID 23627509, compound

Product 1

HCID 58189244HCID 58189244, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-((S)-3-benzyl-piperazin-1-yl)-1-cyclopentyl-3-methyl-1H-indazole (44 mg, 0.12 mmol) in CH2Cl2 (1 mL) was treated with diisopropylethylamine (21 μL, 0.12 mmol) followed by trimethylsilyl isocyanate (31 μL, 0.24 mmol). The reaction mixture was stirred for 16 h after which time an additional equivalent of TMS-isocyanate was added and the reaction mixture was stirred an additional 16 h. The reaction mixture was evaporated and purified by reverse phase HPLC. Product was obtained as a colorless solid (18 mg, 36%). LC/MS (Method B) 3.64 min, [M+1]+ 418.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-c1797aa03dcd4e8681d967e5d4d8c1f8
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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