Diisopropylethylamine → HCID 86687074, compound

HRID 1402220Notes

Reaction equation

HRID 1402220 reaction equation
[CH:1]([Si:4]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[O:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:18]3[CH:19]=[C:20]([O:23][C@H:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[C@@H:27]([NH2:34])[CH2:26][CH2:25]4)[CH:21]=[CH:22][C:17]3=[N:16][N:15]=2)[CH2:10][CH2:9]1)([CH3:3])[CH3:2].ClC(Cl)(Cl)C[O:44][C:45](=O)[NH:46][C:47]1[N:48]([C:56]2[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=2)[N:49]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:51]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[C:52]([C:50]1[CH:51]=[C:47]([NH:46][C:45]([NH:34][C@@H:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:24]([O:23][C:20]3[CH:21]=[CH:22][C:17]4[N:18]([C:14]([N:11]5[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][O:5][Si:4]([CH:35]([CH3:37])[CH3:36])([CH:1]([CH3:2])[CH3:3])[CH:38]([CH3:40])[CH3:39])[CH2:13][CH2:12]5)=[N:15][N:16]=4)[CH:19]=3)[CH2:25][CH2:26]2)=[O:44])[N:48]([C:56]2[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=2)[N:49]=1)([CH3:55])([CH3:53])[CH3:54]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 86687073(1S,4R)-4-[3-(4-Triisopropylsilanyloxyethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine

Product 1

HCID 86687074HCID 86687074, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Intermediate 66c (178 mg, 0.316 mmol) and (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Synthetic Communications, 2009, 39, 3999-4009, which is incorporated herein by reference in its entirety; 128 mg, 0.316 mmol) in 1,4-dioxane (3 mL) and DIPEA (83 μL, 0.474 mmol) was stirred at 95° C. for 4 h. The cooled mixture was concentrated in vacuo. The residue was purified by FCC, using 0-10% MeOH in DCM, to give the title compound as a brown foam (208 mg, 81%). LCMS (Method 3): Rt 5.96 min, m/z 819 [MH+].

Workup

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-d82a71c8611948b4a32472fd935de90b
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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