tert-Butyl isocyanate → HCID 58746658, compound

HRID 724653Notes

Reaction equation

HRID 724653 reaction equation
FC(F)(F)C(O)=O.[O:8]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH:31]3[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]3)=[CH:27][CH:26]=2)=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:39]([N:43]=[C:44]=[O:45])([CH3:42])([CH3:41])[CH3:40]>CN1CCCC1=O.C(N(CC)C(C)C)(C)C>[C:39]([NH:43][C:44](=[O:45])[N:23]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]2)=[CH:27][CH:26]=1)[CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:20][CH:19]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 21878751HCID 21878751, compound

Product 1

HCID 58746658HCID 58746658, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

5-[4-([2-(4-Phenoxyphenyl)ethyl]aminomethyl)phenyl]isothiazolidin-3-one 1,1-dioxide trifluoroacetate (6.5 mg, 0.012 mmol) was dissolved in N-methyl-pyrrolidinone (100 μL) with N,N-diisopropylethylamine (10 μL). A solution of t-butylisocyanate in N-methyl-pyrrolidinone (100 μL) was added and the mixture stirred for 1 h. The mixture was purified by preparative LCMS to give the desired product. White solid, (6.5 mg, 100%). LCMS found for C22H21N2O5S (M+H)+: m/z=536.

Workup

  1. customThe mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-04dfa72b6b2c4a909998f5e34a0a7336
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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