Diisopropylethylamine → benzo[b]thiophene-2-carboxylic Acid (4-tert-butylcyclohexyl)-[4-(2H-tetrazol-5-ylcarbamoyl)benzyl]amide

HRID 1633976Notes

Reaction equation

[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][CH2:12][C:13]2[CH:26]=[CH:25][C:16]([C:17]([NH:19][C:20]3[N:21]=[N:22][NH:23][N:24]=3)=[O:18])=[CH:15][CH:14]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[S:27]1[C:31]([C:32](O)=[O:33])=[CH:30][C:29]2[CH:35]=[CH:36][CH:37]=[CH:38][C:28]1=2.C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17](=[O:18])[NH:19][C:20]3[N:21]=[N:22][NH:23][N:24]=3)=[CH:25][CH:26]=2)[C:32]([C:31]2[S:27][C:28]3[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=3[CH:30]=2)=[O:33])[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To the above resin bound 4-[(4-tert-butylcyclohexylamino)methyl]-N-(2H-tetrazol-5-yl)-benzamide was added a solution of benzo[b]thiophene-2-carboxylic acid (400 μmol) in a mixture of NMP, DCP and diisopropylethylamine (4.5:4.5:1, 1 mL) followed by a solution of PyBrOP (400 μmol) in DCP (500 μL). The mixture was allowed to react 3 hours at 50° C. The resin was cooled to 25° C. while washed with NMP (4×1 mL), and DCM (10×1 mL).

Workup

customto react 3 hours at 50° C
washwhile washed with NMP (4×1 mL), and DCM (10×1 mL)

Sources & evidence

ORD record: ord-2afc91b2f882430facf8de2146485e63
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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