Acetic Acid → HCID 178513918, compound

HRID 403193Notes

Reaction equation

HRID 403193 reaction equation
Br.C(O)(=[O:4])C.C([O:9][C:10]1[C:18]2[C:17]([C:19]3[CH:20]=[N:21][N:22]([CH:24]([CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:25][C:26]#[N:27])[CH:23]=3)=[N:16][C:15]([O:33]C)=[N:14][C:13]=2[NH:12][CH:11]=1)(=O)C>>[CH:28]1([C@H:24]([N:22]2[CH:23]=[C:19]([C:17]3[C:18]4[C:10](=[O:9])[CH2:11][NH:12][C:13]=4[N:14]=[C:15]([OH:33])[N:16]=3)[CH:20]=[N:21]2)[CH2:25][C:26]([NH2:27])=[O:4])[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 670946744-[1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl]-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl acetate

Product 1

HCID 178513918HCID 178513918, compound

Procedure

4 M of HBr in acetic acid (2 mL, 8 mmol) was added to 4-[1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl]-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl acetate (0.050 g, 0.13 mmol) and the reaction was stirred for 1 h. Volatiles were removed in vacuo. The residue was reconstituted and preparative HPLC-MS (eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) was used to afford purified product (12 mg, 26%). 1H NMR (500 MHz, d6-DMSO): δ 9.20 (s, 1H), 8.69 (s, 1H), 7.34 (s, 1H), 6.75 (s, 1H), 4.49 (dt, 1H), 3.89 (s, 2H), 2.80 (dd, 1H), 2.64 (dd, 1H), 2.36-2.26 (m, 1H), 1.83-1.74 (m, 1H), 1.63-1.36 (m, 4H), 1.32-1.20 (m, 2H), 1.15-1.05 (m, 1H); LCMS (M+H)+: 357.0.

Workup

  1. customVolatiles were removed in vacuo
  2. washpreparative HPLC-MS (eluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
  3. customto afford
  4. custompurified product (12 mg, 26%)

Sources & evidence

ORD record
ord-3d76a8567c90433cb9e7d005415f0c3a
Source dataset
uspto-grants-2014_06
Patent number
US08748401B2

Reaction notes

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