1-Boc-3-aminopyrrolidine → HCID 57461720, compound

HRID 1896654Notes

Reaction equation

HRID 1896654 reaction equation
[C:1]([C:4]1[N:8]([CH:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:7]=[N:6][C:5]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)(=O)[CH3:2].C(C1N(C2CN(C(OC(C)(C)C)=O)C2)C=NC=1C1C=CC(F)=CC=1)(=O)C.NC1CCN(C(OC(C)(C)C)=O)C1.[NH2:67][C:68]1[N:73]=C(C2N(C3CN(C(OC(C)(C)C)=O)C3)C=NC=2C2C=CC(F)=CC=2)C=[CH:70][N:69]=1>>[NH2:73][C:68]1[N:67]=[C:1]([C:4]2[N:8]([CH:9]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]3)[CH:7]=[N:6][C:5]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:2]=[CH:70][N:69]=1

Participants

5

Reactant 4

HCID 27563701-Boc-3-aminopyrrolidineHCID 57461719HCID 57461719, compoundHCID 57461730tert-Butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylateHCID 58235103HCID 58235103, compound

Product 1

HCID 57461720HCID 57461720, compound

Procedure

tert-Butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate [C16, prepared according to the general procedure for the synthesis of tert-butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C3) in Example 1, except that tert-butyl 3-aminopyrrolidine-1-carboxylate was used in place of tert-butyl 3-aminoazetidine-1-carboxylate; NMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 2.13 (s, 3H), 2.22 (m, 1H), 2.45 (m, 1H), 3.47-3.88 (m, 4H), 5.55 (m, 1H), 7.15 (dd, J=8.7, 8.7 Hz, 2H), 7.46 (dd, J=8.7, 5.4 Hz, 2H), 7.69 (br s, 1H)] was subjected to reaction conditions similar to those used for preparation of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C4) in Example 1, to provide the product as a solid. Yield: 6.1 g, 14.4 mmol, 67%. 1H NMR (400 MHz, CD3OD) δ 1.48 (s, 9H), 2.32-2.50 (m, 2H), 3.48-3.65 (m, 3H), 3.81 (m, 1H), 5.42 (m, 1H), 6.42 (d, J=4.9 Hz, 1H), 7.09 (dd, J=8.7, 8.7 Hz, 2H), 7.43 (dd, J=8.5, 5.3 Hz, 2H), 7.92 (s, 1H), 8.13 (d, J=4.5 Hz, 1H).

Workup

  1. customNMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 2.13 (s, 3H), 2.22 (m, 1H), 2.45 (m, 1H), 3.47-3.88 (m, 4H), 5.55 (m, 1H), 7.15 (dd, J=8.7, 8.7 Hz, 2H), 7.46 (dd, J=8.7, 5.4 Hz, 2H), 7.69 (br s, 1H)] was subjected to reaction conditions similar to

Sources & evidence

ORD record
ord-e1802dfed78a44978ae45746088765a4
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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