Cyclopropanesulfonamide → HCID 53244366, compound

HRID 1805375Notes

Reaction equation

HRID 1805375 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[N: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:6]4[N: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][CH:7]=4)[C:21]3=[O:20])[CH2:31]2)=[CH:39][CH:38]=1)#[N:37]

Participants

4

Reactant 3

HCID 15765418CyclopropanesulfonamideHCID 21471714Methyl 6-(bromomethyl)pyridine-2-carboxylateHCID 67233302HCID 67233302, compound

Product 1

HCID 53244366HCID 53244366, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from methyl-6-(bromomethyl)picolinate, cyclopropanesulfonamide and (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 C27H22N4O4S: 498, observed (M+H)+: 499.2 1HNMR (400 MHz, DMSO-d6) δppm 1.02-1.15 (m, 2 H) 1.14-1.24 (m, 2 H) 2.08-2.20 (m, 1 H) 2.43-2.48 (m, 1 H) 2.99-3.15 (m, 1 H) 3.27-3.34 (m, 1 H) 5.19 (s, 2 H) 6.14 (d, 1 H) 6.72 (t, 1 H) 6.99 (d, 1H) 7.09 (t, 1 H) 7.47 (d, 1 H) 7.59 (d, 2 H) 7.79 (d, 2 H) 7.92-8.06 (m, 2 H).

Sources & evidence

ORD record
ord-fdf6119f77a644b0907ee8cc24701464
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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