1,4-Dioxane → HCID 178478577, compound

HRID 2375858Notes

Reaction equation

HRID 2375858 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:33][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[NH:28][N:27]=[C:26]5[Cl:32])[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1>Cl>[ClH:32].[ClH:32].[ClH:32].[Cl:32][C:26]1[C:25]2[C:29](=[CH:30][CH:31]=[C:23]([NH:22][C:21]3[C:16]4[CH:15]=[C:14]([C:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=5)[NH:33][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:24]=2)[NH:28][N:27]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 1784517324-[4-(3-Chloro-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178478577HCID 178478577, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 4-[4-(3-chloro-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (45.4 mg, 0.0945 mmol, 1 eq) in 4.0 M of HCl in 1,4-dioxane (3.25 mL, 140 eq) was allowed to stir at rt for 2 h. The reaction was concentrated in vacuo to dryness, affording the title compound, as a yellow solid. 1H NMR (400 MHz, MeOH-d4): δ=2.83 (s, br, 2H), 3.52 (t, J=6.0 Hz, 2H), 3.95 (s, br, 2H), 6.44 (s, 1H), 6.83 (s, br, 1H), 7.56 (d, J=8.8 Hz, 1H), 7.75 (dd, J=8.8, 0.8 Hz, 1H), 8.19 (s, 1H), 8.28 (d, J=0.8 Hz, 1H). MS (ES+): m/z 365.98/368.00 (20/8) [MH+]. HPLC: tR=0.48 & 1.56 min (ZQ2000, polar—5 min).

Workup

  1. concentrationThe reaction was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-3ae35cbcfb5e4e26afb9d09194085d0f
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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