tert-Butanol → HCID 57593699, compound

HRID 1785306Notes

Reaction equation

HRID 1785306 reaction equation
[Cl:1][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[NH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[C:23]([Br:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]2[CH:27]=[C:28]([NH:32][C:33]([N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[O:34])[CH:29]=[CH:30][CH:31]=2)[N:19]=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7].[NH2:5][S:2]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[C:23]([Br:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]2[CH:27]=[C:28]([NH:32][C:33]([N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[O:34])[CH:29]=[CH:30][CH:31]=2)[N:19]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanateHCID 81531DiisopropylethylamineHCID 57593297HCID 57593297, compound

Product 2

HCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 57593699HCID 57593699, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Chloro[[(1,1-dimethylethoxy)carbonyl]amino]-sulfane dioxide was prepared by adding chlorosulfonyl isocyanate (32 mg, 0.23 mmol, 1.0 eq.) to a cooled solution of tert-butyl alcohol (17 mg, 0.23 mmol, 1.0eq.) and dichloromethane (2 mL) in an ice-water bath. The resulting mixture was stirred at 0-5° C. for 2-3 hr. The solution was then treated with a solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (100 mg, 0.20 mmol, 1eq.) and dichloromethane (5 mL). DMAP (20 mg, 0.16 mmol) was then added followed by the dropwise addition of DIEA (0.1 mL, 0.57 mmol). The mixture was stirred at RT for overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in TFA (2 mL), and purified by HPLC using acetonitrile/water to afford the title compound (30 mg).

Workup

  1. stirringThe mixture was stirred at RT for overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in TFA (2 mL)
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-8cc5d5ff710a4e5c8fc9fd4d32199cdd
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

Loading…