Hydrochloric Acid → HCID 69275387, compound

HRID 2375930Notes

Reaction equation

HRID 2375930 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH:13]=[C:12]([C:15]2[NH:34][C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[N:29]([CH3:33])[N:28]=[CH:27]5)[C:17]=3[CH:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[CH3:33][N:29]1[C:30]2[C:26](=[CH:25][C:24]([NH:23][C:22]3[C:17]4[CH:16]=[C:15]([C:12]5[CH2:13][CH2:14][NH:9][CH2:10][CH:11]=5)[NH:34][C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:32][CH:31]=2)[CH:27]=[N:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11626469HCID 11626469, compound

Product 1

HCID 69275387HCID 69275387, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (4.7 mL; 20 eq) was added to a suspension of 4-[4-(1-methyl-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (415.4 mg, 0.9324 mmol, 1 eq) in 1,4-dioxane (8 mL) and stirred at rt for 2 h. The solid was filtered off, washed several times with dioxane, and dried under vacuum, yielding the title compound, as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.65 (s, br, 2H), 3.32 (s, br, 2H), 3.80 (s, br, 2H), 4.11 (s, 3H), 6.50 (s, 1H), 7.04 (s, br, 1H), 7.51 (dd, J=8.8, 1.6 Hz, 1H), 7.83 (d, J=9.2 Hz, 1H), 7.98 (s, 1H), 8.15 (s, 1H), 8.26 (s, 1H), 9.43 (s, br, —NH+—NH), 11.56 (s, br, —NH), 13.09 (s, H+). MS (ES+): m/z 346.16 (31) [MH+]. HPLC: tR=1.57 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed several times with dioxane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-638aeb6272944f53a7d142a7a6d2d749
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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