Tert-Butanesulfinamide → (R)-N-(5-((R)-t-butylsulfinylamino(2-chlorophenyl)methyl)thiazol-2-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 1855223Notes

Reaction equation

HRID 1855223 reaction equation
CC(S(N)=O)(C)C.O1C2C=CC(C3(C(O)=O)CC3)=CC=2OC1.[C:23]([S@@:27]([NH:29][C@H:30]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[Cl:57])[C:31]1[S:35][C:34]([NH:36][C:37]([C:39]2([C:42]3[CH:50]=[CH:49][C:45]4[O:46][CH2:47][O:48][C:44]=4[CH:43]=3)[CH2:41][CH2:40]2)=[O:38])=[N:33][CH:32]=1)=[O:28])([CH3:26])([CH3:25])[CH3:24]>CC#N>[C:23]([S@:27]([NH:29][C@H:30]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[Cl:57])[C:31]1[S:35][C:34]([NH:36][C:37]([C:39]2([C:42]3[CH:50]=[CH:49][C:45]4[O:46][CH2:47][O:48][C:44]=4[CH:43]=3)[CH2:40][CH2:41]2)=[O:38])=[N:33][CH:32]=1)=[O:28])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 3382465Tert-ButanesulfinamideHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 86621210(S)-N-(5-((R)-t-butylsulfinylamino(2-chlorophenyl)methyl)thiazol-2-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Product 1

HCID 59757123(R)-N-(5-((R)-t-butylsulfinylamino(2-chlorophenyl)methyl)thiazol-2-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-N-(5-((R)-t-butylsulfinylamino(2-chlorophenyl)methyl)thiazol-2-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide was prepared from (R)-N-(R)-1-(2-aminothiazol-5-yl)-1-(2-chlorophenyl)methyl)-1,1-dimethylethylsulfinamide and 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid using the same protocol for (S)-N-(5-((R)-t-butylsulfinylamino(2-chlorophenyl)methyl)thiazol-2-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide. 1H-NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 7.62 (dd, J=7.7, 1.7 Hz, 1H), 7.37 (d, J=0.7 Hz, 1H), 7.34 (dd, J=7.8, 1.4 Hz, 1H), 7.31-7.20 (m, 2H), 6.87 (td, J=8.4, 1.7 Hz, 2H), 6.81 (d, J=7.9 Hz, 1H), 6.30 (d, J=2.8 Hz, 1H), 6.01 (s, 2H), 3.74 (d, J=2.8 Hz, 1H), 1.71-1.68 (m, 2H), 1.24 (s, 9H), 0.88 (t, J=6.9 Hz, 2H). HPLC ret. time 3.59 min, 10-99% CH3CN, 5 min run; ESI-MS 532.1 m/z (MH+).

Sources & evidence

ORD record
ord-1253f3182942430eae1be254abebde52
Source dataset
uspto-grants-2015_02
Patent number
US08962856B2

Reaction notes

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