Methyl N-(triethylammoniosulfonyl)carbamate → HCID 59568585, compound

HRID 216971Notes

Reaction equation

HRID 216971 reaction equation
[NH2:1][C:2](=O)[C@@H:3]([NH:27][C:28]([C:30]1([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:2]([C@@H:3]([NH:27][C:28]([C:30]1([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)#[N:1]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568627HCID 59568627, compound

Product 1

HCID 59568585HCID 59568585, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4′-(4-methylpiperazin-1-ylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 29, step (i), 267 mg) in dichloromethane (10 mL) was treated with Burgess' reagent (202 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated under reduced pressure and the mixture was purified by chromatography on silica eluting with methanol/dichloromethane (0:100 to 5:95), triethylamine/methanol/dichloromethane (1:5:95) to afford the sub-titled compound (250 mg).

Workup

  1. customThe solvent was partially evaporated under reduced pressure
  2. customthe mixture was purified by chromatography on silica eluting with methanol/dichloromethane (0:100 to 5:95), triethylamine/methanol/dichloromethane (1:5:95)

Sources & evidence

ORD record
ord-e39a55fa601d45c3bd23985a540f824e
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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