Ammonium Hydroxide → HCID 67005159, compound

HRID 564405Notes

Reaction equation

HRID 564405 reaction equation
[CH2:1]([O:3][C@@H:4]1[CH2:8][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6][C@H:5]1[NH2:15])[CH3:2].[F:16][C:17]([F:32])([F:31])[C:18]1[CH:19]=[C:20]([CH:28]=[CH:29][CH:30]=1)[C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[OH-]>C(Cl)Cl.CCOC(C)=O.CO>[CH2:1]([O:3][C@@H:4]1[CH2:8][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6][C@H:5]1[NH:15][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[C:20]1[CH:28]=[CH:29][CH:30]=[C:18]([C:17]([F:16])([F:32])[F:31])[CH:19]=1)[CH3:2]

Participants

10

Reactant 6

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67005267HCID 67005267, compound

Product 1

HCID 67005159HCID 67005159, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of rel-(3R,4R)-4-ethoxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-amine (36 mg, 0.168 mmol) in DCM was added {[3-(trifluoromethyl)benzoyl]amino}acetic acid (41.5 mg, 0.168 mmol), HATU (76.7 mg, 0.202 mmol), HOBt (27.2 mg, 0.202 mmol) and DIPEA (0.044 mL, 0.252 mmol) and was stirred at RT overnight. The resulting crude mixture was subjected to flash chromatography (15% MeOH, 1% NH4OH in EtOAc) to afford the title compound (38 mg, 51%) as a white solid. 1H-NMR (CDCl3) δ: 1.17 (t, J=6.9 Hz, 3H), 1.40-1.60 (m, 2H), 1.65-1.82 (m, 2H), 2.22-2.40 (m, 2H), 2.63-2.80 (m, 2H), 3.22-3.51 (m, 4H), 3.63-3.80 (m, 2H), 3.89-4.00 (m, 2H), 4.10-4.20 (m, 2H), 4.24-4.37 (m, 1H), 6.45-6.58 (m, 1H), 7.20-7.30 (m, 1H), 7.56 (t, J=8.1 Hz, 1H), 7.76 (d, J=7.5 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 8.08 (s, 1H). MS m/z: 444 (M+1).

Sources & evidence

ORD record
ord-6071949f09ca49f0b36c628316e9318f
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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