methyl (1aRS,7bSR)-5-[2-((R)-1-ethyl-pyrrolidin-3-ylmethyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate → Methyl (1aR,7bS)-5-{2-[2-((R)-1-ethylpyrrolidin-2-yl)ethyl]-4-fluoro-benzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 928082Notes

Reaction equation

HRID 928082 reaction equation
C(N1CC[C@@H]([CH2:8][C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[S:16]([NH:19][C:20]2[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]3[C:23]([CH:24]4[CH2:34][CH:25]4[CH2:26][O:27]3)=[CH:22][CH:21]=2)(=[O:18])=[O:17])C1)C.[CH2:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42]CC1C=C(F)C=CC=1S(Cl)(=O)=O)[CH3:36].NC1C(C(OC)=O)=C2C([C@H]3C[C@H]3CO2)=CC=1>>[CH2:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[S:16]([NH:19][C:20]1[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]2[C:23]([C@H:24]3[CH2:34][C@H:25]3[CH2:26][O:27]2)=[CH:22][CH:21]=1)(=[O:17])=[O:18])[CH3:36]

Participants

4

Reactant 3

HCID 71006876methyl (1aRS,7bSR)-5-[2-((R)-1-ethyl-pyrrolidin-3-ylmethyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylateHCID 86713369(1AR,7bS)-methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×HCID 867133762-[2-((R)-1-Ethylpyrrolidin-2-yl)ethyl]-4-fluorobenzenesulfonyl chloride2×

Product 1

HCID 71006893Methyl (1aR,7bS)-5-{2-[2-((R)-1-ethylpyrrolidin-2-yl)ethyl]-4-fluoro-benzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 95, starting from 2-[2-((R)-1-ethyl-pyrrolidin-2-yl)-ethyl]-4-fluorobenzenesulfonyl chloride (intermediate 230) and methyl (1aR,7bS)-5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 42A).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4ee3c58a3ab44e828a6a56c860331ac4
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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