Ethyl Bromide → HCID 67005313, compound

HRID 564416Notes

Reaction equation

HRID 564416 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH:12][CH2:13][C:14]([OH:16])=O.[CH2:19]([O:21][C@@H:22]1[CH2:26][N:25]([CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:24][C@H:23]1[NH:33]C(=O)CC1C(C(F)(F)F)=CC=CC=1C(N)=O)[CH3:20].F[C:51](F)(F)C1C=C(C=CC=1)C(NCC(O)=O)=O.C(Br)C=C.BrCC>>[CH2:19]([O:21][C@@H:22]1[CH2:26][N:25]([CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:24][C@H:23]1[NH:33][C:14](=[O:16])[CH2:13][NH:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:18])[F:17])[CH:4]=2)[NH:8][N:7]=1)[CH:20]=[CH2:51]

Participants

5

Reactant 4

HCID 6332Ethyl BromideHCID 7841Allyl bromideHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 131729297HCID 131729297, compound

Product 1

HCID 67005313HCID 67005313, compound

Procedure

The title compound was synthesized in similar fashion to rel-N-(2-{([(3R,4R)-4-ethoxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide {[5-(trifluoromethyl)-1H-indazol-3-yl]amino}acetic acid was substituted for {[3-(trifluoromethyl)benzoyl]amino}acetic acid, and allyl bromide was substituted for bromoethane, and was isolated as a white solid. 1H-NMR (DMSO-d6) δ: 1.18-1.35 (m, 2H), 1.60-1.70 (m, 2H), 2.06-2.16 (m, 1H), 2.23-2.31 (m, 1H), 2.38-2.44 (m, 1H), 2.74-2.84 (m, 2H), 3.18-3.28 (m, 2H), 3.72-3.87 (m, 6H), 3.92-4.08 (m, 2H), 5.02-5.19 (m, 2H), 5.73-5.87 (m, 1H), 6.70 (t, 1H), 7.39 (d, 1H), 7.48 (dd, 1H), 8.03 (d, 1H), 8.26 (s, 1H), 11.9 (s, 1H). MS m/z: 468 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-1f8d3d1b4d404868a47669c151a219c8
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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