1,1'-Carbonyldiimidazole → HCID 25174484, compound

HRID 2190330Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([Cl:18])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)[N:6]=1.C1N=CN([C:24]([N:26]2[CH:30]=N[CH:28]=[CH:27]2)=[O:25])C=1.CNCC[CH:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:18][C:4]1[S:3][C:2]([NH:1][C:24](=[O:25])[N:26]([CH2:27][CH2:28][CH:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH3:30])=[N:6][C:5]=1[C:7]1[CH:8]=[CH:9][C:10]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of N-(4-(2-amino-5-chlorothiazol-4-yl)phenyl)methanesulfonamide 13 (0.100 g, 0.33 mmol), DMAP (0.056 g, 0.46 mmol), and CDI (0.085 g, 0.52 mmol) was added DMF (0.5 mL). The reaction mixture was heated to 40° C. for 13 h and N-methyl-3,3-diphenylpropan-1-amine 12 (0.111 g, 0.49 mmol) was added. The reaction mixture was heated to 40° C. for 2 d. Direct purification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in DCM), followed by purification by flash column chromatography on silica gel (eluted with 1% to 5% MeOH in DCM) gave 3-(5-chloro-4-(4-(methylsulfonamido)-phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-methylurea 14 as a white foam. Mass spectrum: calculated for C27H27ClN4O3S2 554.2; found 555.2 (M++1).

Workup

temperatureThe reaction mixture was heated to 40° C. for 2 d
customDirect purification by flash column chromatography on silica gel (eluted with 10% to 50% EtOAc in DCM)
customfollowed by purification by flash column chromatography on silica gel (eluted with 1% to 5% MeOH in DCM)

Sources & evidence

ORD record: ord-990293303d6445d194f12e04b292882f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324396B2

Reaction notes

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