Water → HCID 178484269, compound

HRID 2278710Notes

Reaction equation

HRID 2278710 reaction equation
[CH3:1][N:2]([CH2:13][C:14]1[C:15]([C:25]2[CH:33]=[C:32]3[C:28]([CH:29]=[N:30][N:31]3[CH3:34])=[CH:27][CH:26]=2)=[N:16][N:17](C2CCCCO2)[CH:18]=1)[CH2:3][CH2:4][NH:5]C(=O)OC(C)(C)C.C(N(CC)CC)C.O.CC#N>O1CCCC1.Cl>[CH3:1][N:2]([CH2:13][C:14]1[C:15]([C:25]2[CH:33]=[C:32]3[C:28]([CH:29]=[N:30][N:31]3[CH3:34])=[CH:27][CH:26]=2)=[N:16][NH:17][CH:18]=1)[CH2:3][CH2:4][NH2:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 90463304HCID 90463304, compound

Product 1

HCID 178484269HCID 178484269, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl N-[2-[methyl([[3-(1-methyl-1H-indazol-6-yl)-1-(oxan-2-yl)-1H-pyrazol-4-yl]methyl])amino]ethyl]carbamate (50 mg, 0.11 mmol, 1.00 equiv) in tetrahydrofuran (3 mL) and 12N hydrochloric acid (2 mL) was stirred at room temperature overnight. The pH of the solution was adjusted to 7 with triethylamine. The resulting mixture was concentrated and the residue purified by Pre-HPLC with the following conditions (1#-Pre-HPLC-005 (Waters)): Column, XBridge Shield RP18 OBD Column, 5 μm, 19×150 mm; mobile phase, water with 10 mmol NH4HCO3 and CH3CN (18% CH3CN up to 58% in 10 min, up to 95% in 1 min, down to 18% in 2 min); Detector, UV 254/220 nm to give 5 mg (16%) of N1-methyl-N1-((3-(1-methyl-1H-indazol-6-yl)-1H-pyrazol-4-yl)methyl)ethane-1,2-diamine as a light yellow oil. 1H-NMR (300 MHz, CDCl3): δ 8.05 (s, 1H), 7.89-7.84 (m, 2H), 7.73 (s, 1H), 7.54-7.50 (m, 1H), 4.12 (s, 3H), 3.67 (s, 2H), 2.84 (d, J=6.3 Hz, 2H), 2.55 (d, J=6.3 Hz, 2H), 2.27 (s, 3H) ppm. LCMS (method A1, ESI): RT=0.90 min, m/z=285.0 [M+H]+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customthe residue purified by Pre-HPLC with the following conditions (1#-Pre-HPLC-005 (Waters))
  3. waitdown to 18% in 2 min)

Sources & evidence

ORD record
ord-b3928ab1d4a14281aa71abdcc307169a
Source dataset
uspto-grants-2015_09
Patent number
US09133189B2

Reaction notes

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