Methyl 4-(bromomethyl)benzoate → HCID 58305369, compound

HRID 1805376Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[CH:13]1([S:16]([NH2:19])(=[O:18])=[O:17])[CH2:15][CH2:14]1.[O:20]=[C:21]1[C@:29]2([CH2:31][C@@H:30]2[C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22]1>>[C:36]([C:35]1[CH:34]=[CH:33][C:32]([C@H:30]2[C@@:29]3([C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH2:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([NH:19][S:16]([CH:13]5[CH2:15][CH2:14]5)(=[O:18])=[O:17])=[O:12])=[CH:9][CH:8]=4)[C:21]3=[O:20])[CH2:31]2)=[CH:39][CH:38]=1)#[N:37]

Participants

Reactant 3

HCID 256687Methyl 4-(bromomethyl)benzoate

HCID 15765418Cyclopropanesulfonamide

HCID 67233302HCID 67233302, compound

Product 1

HCID 58305369HCID 58305369, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 4-bromomethyl-benzoic acid methyl ester, cyclopropanesulfonamide (commercially available), (1R,2S) and (1S,2R)-4-(2′-oxospiro[cyclopropane-1,3′-indoline]-2-yl)benzonitrile prepared as in Scheme 1. LC/MS m/e calcd. for C28H23ClN3O4S: 497, observed (M+H)+: 498.2, 1H NMR (400 MHz, DMSO-d6) δppm 0.69-0.79 (m, 2 H) 0.83-0.92 (m, 2 H) 2.11-2.18 (m, 1 H) 2.44-2.49 (m, 1 H) 2.91-3.00 (m, 1 H) 3.12-3.20 (m, 1 H) 3.27-3.32 (m, 1 H) 5.04 (s, 2 H) 6.15 (d, 1 H) 6.68 (t, 1 H) 6.91 (d, 1 H) 7.02-7.09 (m, 2 H) 7.28-7.37 (m, 2 H) 7.50-7.59 (m, 2 H) 7.77-7.82 (m, 2H) 7.87-7.94 (m, 2 H).

Sources & evidence

ORD record: ord-58465418af3543c49e91107f17d2ae4a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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