Triethylamine → (R)-tert-Butyl 3-((2S,4S)-1-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6-morpholino-1,3,5-triazin-2-yl)-4-methoxypyrrolidine-2-carboxamido)piperidine-1-carboxylate

HRID 1961410Notes

Reaction equation

HRID 1961410 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:13]=[C:12]([N:22]4[CH2:26][C@@H:25]([O:27][CH3:28])[CH2:24][C@H:23]4[C:29](O)=[O:30])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[NH2:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][N:47]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:46]1.O.N1(O)C2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:13]=[C:12]([N:22]4[CH2:26][C@@H:25]([O:27][CH3:28])[CH2:24][C@H:23]4[C:29]([NH:44][C@@H:45]4[CH2:50][CH2:49][CH2:48][N:47]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:46]4)=[O:30])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59436437(2S,4S)-1-(4-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-6-morpholino-1,3,5-triazin-2-yl)-4-methoxypyrrolidine-2-carboxylic acid

Product 1

HCID 59436378(R)-tert-Butyl 3-((2S,4S)-1-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6-morpholino-1,3,5-triazin-2-yl)-4-methoxypyrrolidine-2-carboxamido)piperidine-1-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 112B (900 mg, 1.653 mmol) in DMF (10 ml) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (951 mg, 4.96 mmol), (R)-tert-butyl 3-aminopiperidine-1-carboxylate (993 mg, 4.96 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (253 mg, 1.653 mmol), and Et3N (1.382 ml, 9.92 mmol). The reaction mixture was stirred at RT for 14 h. The crude reaction mixture was purified by prep. HPLC to give 112C (800 mg, 79%). LC/MS [M+H]+: 613; Ret time (Method F): 2.99 min.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by prep

Sources & evidence

ORD record
ord-0fa755ab9e344469963c1800caca27b5
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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