Dimethylformamide → HCID 178422732, compound

HRID 1898372Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23](O)=[O:24])=[CH:14][C:12]=2[N:13]=1.F[B-](F)(F)F.[N:32]1(OC(N(C)C)=[N+](C)C)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.[CH3:49]N(C=O)C.[CH2:54]1[CH2:58]OC[CH2:55]1>>[C:36]12([NH:32][C:23]([C:15]3[C:16]4[O:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]=4[C:11]4[NH:10][C:9]([NH:8][C:7]5[C:6]([Cl:26])=[CH:5][N:4]=[CH:3][C:2]=5[Cl:1])=[N:13][C:12]=4[CH:14]=3)=[O:24])[CH2:55][CH:54]3[CH2:58][CH:38]([CH2:39][CH:40]([CH2:49]3)[CH2:35]1)[CH2:37]2

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8028Tetrahydrofuran

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 178422814HCID 178422814, compound

Product 1

HCID 178422732HCID 178422732, compound

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-3, 0.080 g, 0.203 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.130 g, 0.406 mmol), TEA (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and adamantly amine (0.092 g, 0.609 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.49 (s, 6H), 1.66 (s, 6H), 2.01 (s, 9H), 3.01 (s, 2H), 7.19 (s, 1H), 7.51 (s, 1H), 8.42 (s, 2H), 10.87 (s, 1H), 11.39 (s, 1H); MS [M+H]+: 526.38.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-e9a9bd127b0c4691b4c2277956f2b4e2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519149B2

Reaction notes

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