1-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester → (1R,2S)-1-{[(2S,4R)-1-{(1S)-1-[(S)-(Cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

HRID 1822457Notes

Reaction equation

HRID 1822457 reaction equation
C([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])C.C(OC(C1(NC(C2CC(OC3C4C(=CC(OC)=CC=4)N=C(C4C=CC=CC=4)C=3)CN2[C:75](=[O:95])[NH:76][CH:77]([C:82](=[O:94])[NH:83][CH:84]2[C:92]3[C:87](=[CH:88][CH:89]=[CH:90][CH:91]=3)C[CH:85]2[OH:93])[C:78]([CH3:81])([CH3:80])[CH3:79])=O)CC1C=C)=O)C.OC1CC2C(=CC=CC=2)[CH:98]1[NH:106]C(C(N1CC(OC2C3C(=CC(OC)=CC=3)C=C(C3C=CC=CC=3)C=2)CC1C1(C(O)=O)CC1C=C)C(C)(C)C)=O>>[CH:92]1([C@H:84]([NH:83][C:82]([C@@H:77]([NH:76][C:75]([N:15]2[CH2:16][C@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:18][C@H:14]2[C:12]([NH:11][C@:6]2([C:4]([OH:3])=[O:5])[CH2:8][C@H:7]2[CH:9]=[CH2:10])=[O:13])=[O:95])[C:78]([CH3:79])([CH3:80])[CH3:81])=[O:94])[C:85](=[O:93])[NH:106][CH3:98])[CH2:91][CH2:90][CH2:89][CH2:88][CH2:87]1

Participants

4

Reactant 3

HCID 207653161-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 684916281-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 68493461HCID 68493461, compound

Product 1

HCID 49771834(1R,2S)-1-{[(2S,4R)-1-{(1S)-1-[(S)-(Cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acidYield 18%

Procedure

Compound 12 was treated as described for the preparation of 13 but with the use of 21 instead of 2-amino-N-(2-hydroxy-indan-1-yl)-3,3-dimethyl-butyramide followed by ester hydrolysis as described for the preparation of compound 14 which, after purification by HPLC, gave the title compound (8.6 mg, 18% yield). Purity by HPLC >95%. M+H+783.3.

Workup

  1. customafter purification by HPLC

Sources & evidence

ORD record
ord-1a8d28602fee482cb554bd3b5c13c8b1
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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