HCID 11690537, compound → HCID 11508914, compound

HRID 2375816Notes

Reaction equation

HRID 2375816 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1>Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

3

Reactant 1

HCID 11690537HCID 11690537, compound

Product 1

HCID 11508914HCID 11508914, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Alternative solvents for removal of the Boc group include, but are not limited to, MeOH and water, as demonstrated here with EXAMPLE 45: A suspension of tert-butyl 4-[4-(1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (670 mg, 1.55 mmol) in 4 N HCl (aq) (20 mL) was stirred at rt for 18 h. The precipitates were collected by filtration and washed with ether (3×10 mL) to afford (1H-indazol-5-yl)-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine as tri-HCl salt. 1H-NMR (DMSO-d6, 400 MHz): δ=2.63 (m, 2H), 3.30 (m, 2H), 3.79 (m, 2H), 6.52 (s, br, 1H), 7.44 (dd, J=2.0, 8.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.95 (s, 1H), 8.18 (d, J=1.2 Hz, 1H), 8.26 (s, 1H), 9.59 (s, 1H). MS (ES+): m/z 332.12 [MH+]. HPLC: tR=0.44 and 1.37 min (ZQ2000, polar—5 min).

Workup

  1. customAlternative solvents for removal of the Boc group
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with ether (3×10 mL)

Sources & evidence

ORD record
ord-21bae48a6edd465f8930cde6aa185173
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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