Dimethylformamide → 3-(Benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-isopropylurea

HRID 2190326Notes

Reaction equation

HRID 2190326 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH2:22].[CH:23]([NH:26][CH2:27][CH2:28][CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:25])[CH3:24].CN(C=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[NH:22][C:6](=[O:7])[N:26]([CH2:27][CH2:28][CH:29]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:23]([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8706Benzo(d)thiazol-2-amineHCID 682631,1'-CarbonyldiimidazoleHCID 20540373N-isopropyl-3,3-diphenylpropan-1-amine

Product 1

HCID 251343143-(Benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-isopropylureaYield 65.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of CDI (0.146 g, 0.900 mmol) and DMAP (small catalytic amount) in DCM (1.3 mL) at room temperature was added benzo[d]thiazol-2-amine 3 (0.101 g, 0.672 mmol). The reaction mixture was stirred at room temperature for 1 d and N-isopropyl-3,3-diphenylpropan-1-amine 2 (0.213 g, 0.841 mmol) and DMF (0.5 mL) were added. The reaction mixture was stirred at room temperature for 3 d. Direct purification by flash column chromatography on silica gel (eluted with 50% to 100% DCM in hexanes) gave 3-(benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-isopropylurea 4 (0.190 g) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 d
  2. customDirect purification by flash column chromatography on silica gel (eluted with 50% to 100% DCM in hexanes)

Sources & evidence

ORD record
ord-10151e58573241459178486c078e1088
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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