(S,S) {2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester → ((S)-1-{(S)-2-[4-(6-bromo-thieno[3,2-b]thiophen-3-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

HRID 716544Notes

Reaction equation

[Br:1][C:2]1[C:6]2[S:7][CH:8]=[C:9]([C:10]3[N:11]=[C:12]([C@@H:15]4[CH2:19][CH2:18][CH2:17][NH:16]4)[NH:13][CH:14]=3)[C:5]=2[S:4][CH:3]=1.[CH3:20][O:21][C:22](=[O:79])[NH:23][C@H:24]([C:28](N1CCC[C@H]1C1NC(C2C=CC(C3SC4=NC(NC([C@@H]5CCCN5C(=O)[C@H](NC(OC(C)(C)C)=O)C5C=CC=CC=5)=O)=CN4C=3)=CC=2)=CN=1)=[O:29])[CH:25]([CH3:27])[CH3:26].C(OC(=O)N[C@@H](C1C=CC=CC=1)C(N1CCC[C@H]1C(=O)NC1N=C2N(C=1)C=C(Br)S2)=O)(C)(C)C>>[CH3:20][O:21][C:22](=[O:79])[NH:23][C@H:24]([C:28]([N:16]1[CH2:17][CH2:18][CH2:19][C@H:15]1[C:12]1[NH:13][CH:14]=[C:10]([C:9]2[C:5]3[S:4][CH:3]=[C:2]([Br:1])[C:6]=3[S:7][CH:8]=2)[N:11]=1)=[O:29])[CH:25]([CH3:27])[CH3:26]

Participants

Reactant 3

HCID 67241361(S,S) {2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

HCID 86678452(S,S,S,R)-[1-(2-{5-[4-(6-{[1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carbonyl]-amino}imidazo[2,1-b]thiazol-2-yl)-phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HCID 178419471HCID 178419471, compound

Product 1

HCID 178502408((S)-1-{(S)-2-[4-(6-bromo-thieno[3,2-b]thiophen-3-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Procedure

Compound 78 was synthesized from compound 77 (1.56 mmol) and compound 1 (1.64 mmol), following the procedure as described for compound 23 to give compound 78 in 82% yield. MS (ESI, EI+) m/z=513.2/515 (MH+).

Sources & evidence

ORD record: ord-e99ab67f5b0e426e8899454339d241ac
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187496B2

Reaction notes

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