Ammonia → HCID 57812621, compound

HRID 912011Notes

Reaction equation

HRID 912011 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH:9]=[C:8]([C:11]3[C:15]4[CH:16]=[N:17][C:18]([NH2:32])=[C:19]([O:20][C@@H:21]([C:23]5[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=5[Cl:31])[CH3:22])[C:14]=4[O:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:2]1.C[Si]([N:37]=[C:38]=[O:39])(C)C.CN(C=O)C.CCN(C(C)C)C(C)C.N>CO>[NH2:32][C:18]1[N:17]=[CH:16][C:15]2[C:11]([C:8]3[CH2:7][CH2:6][N:5]([CH:3]4[CH2:2][N:1]([C:38]([NH2:37])=[O:39])[CH2:4]4)[CH2:10][CH:9]=3)=[CH:12][O:13][C:14]=2[C:19]=1[O:20][C@@H:21]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=1[Cl:31])[CH3:22]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 57812413HCID 57812413, compound

Product 1

HCID 57812621HCID 57812621, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(1-Azetidin-3-yl-1,2,3,6-tetrahydropyridin-4-yl)-7-[(R)-1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0209 mmol), trimethylsilyl isocyanate (4.25 μL, 0.0314 mmol), DMF (1.0 mL, 13 mmol) and DIPEA (7.30 μL, 0.0419 mmol) were mixed together and stirred at room temperature for 1 hour. The crude was passed through SCX-2 SPE and the product was release by 2 M NH3 in methanol for MDP purification. MS (ES+): m/z 555.05/557.04 (100/76) [MH+]. HPLC: tR=0.55 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, CD3OD): δ=1.88 (d, J=6.8 Hz, 3H), 2.56 (br. s., 2H), 2.67-2.73 (m, 2H), 3.15-3.22 (m, 2H), 3.34-3.42 (m, 1H), 3.89 (dd, J=8.6, 5.3 Hz, 2H), 4.01-4.09 (m, 2H), 6.27 (br. s., 1H), 6.50 (q, J=6.7 Hz, 1H), 7.21 (t, J=8.6 Hz, 1H), 7.40 (dd, J=9.0, 4.9 Hz, 1H), 7.63 (s, 1H), 8.19 (s, 1H).

Workup

  1. customfor MDP purification

Sources & evidence

ORD record
ord-8811d704c4b04e2a995e03fa3025c617
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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