Bromomethylcyclopropane → HCID 58867422, compound

HRID 2426704Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][CH2:25][C@@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]3)=[C:18]([F:30])[CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6]C=CC=1.CN(C)[C@@H]1CCN(C2C=CC(NC(=O)C3C=CC(O)=CC=3)=CC=2F)C1.C1(CBr)CC1>>[CH:2]1([CH2:1][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:26][CH2:25][C@@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]4)=[C:18]([F:30])[CH:17]=3)=[O:14])=[CH:31][CH:32]=2)[CH2:7][CH2:6]1

Participants

Reactant 3

HCID 81503Bromomethylcyclopropane

HCID 67148105HCID 67148105, compound

HCID 67148281HCID 67148281, compound

Product 1

HCID 58867422HCID 58867422, compound

Procedure

(R)-4-Benzyloxy-N-[4-(3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]benzamide underwent debenzylating hydrogenation by method B. The resulting (R)-N-[4-(3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-4-hydroxybenzamide was alkylated with cyclopropylmethyl bromide by method H. This resulted in the product with the molecular weight of 397.50 (C23H28N3O2); MS (ESI): 398 (M+H+). The following examples were likewise obtained by method H:

Workup

customThis resulted in the product with the molecular weight of 397.50 (C23H28N3O2)

Sources & evidence

ORD record: ord-c0778b8d071b4c07aa7c3de709b92e70
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968550B2

Reaction notes

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