Tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate → HCID 118045101, compound

HRID 525718Notes

Reaction equation

HRID 525718 reaction equation
Cl[C:2]1[C:21]([C:22]2[N:26](C3CCCCO3)[N:25]=[CH:24][CH:23]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH2:33]1[C:36]2([CH2:40][CH2:39][NH:38][CH2:37]2)[CH2:35][N:34]1C(OC(C)(C)C)=O>>[Cl:19][C:16]([F:18])([F:17])[O:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:20]=[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)[C:2]([N:38]3[CH2:39][CH2:40][C:36]4([CH2:33][NH:34][CH2:35]4)[CH2:37]3)=[N:3][CH:4]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 49757941Tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylateHCID 867026376-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 118045101HCID 118045101, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 33 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide (Stage 48.2) and tert-butyl 2,6-diazaspiro[3.4]octane-2-carboxylate to afford an off-white powder. UPLC-MS (Condition 3) tR=0.79 min, m/z=475.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.04 (t, J=6.65 Hz, 2H) 3.14 (d, J=4.69 Hz, 3H) 3.46 (s, 2H) 3.76 (q, J=10.04 Hz, 4H) 6.39 (s, 1H) 7.31 (d, J=8.60 Hz, 2H) 7.78-7.92 (m, 3H) 8.08 (br. s, 1H) 8.74 (br. s, 1H) 10.27 (s, 1H) 12.90-13.01 (m, 1H).

Workup

  1. customto afford an off-white powder

Sources & evidence

ORD record
ord-0746966086e940f7a1d7f22d76cf0131
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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