Hydrochloric Acid → HCID 136352320, compound

HRID 1046487Notes

Reaction equation

HRID 1046487 reaction equation
C([N:4]1[CH:8]=[C:7]([C:9]2[C:13]3[C:14]([O:18][CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]=2)[CH:6]=[C:5]1[C:44]([O:46]C)=[O:45])(C)C.[Li+].[OH-].Cl.[CH2:51]1[CH2:55]OC[CH2:52]1>>[CH:51]([C:5]1([C:44]([OH:46])=[O:45])[CH2:6][C:7]([C:9]2[C:13]3[C:14]([O:18][CH:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]=2)=[CH:8][NH:4]1)([CH3:55])[CH3:52]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66825313HCID 66825313, compound

Product 1

HCID 136352320HCID 136352320, compoundYield 97%

Procedure

Methyl 1-isopropyl-4-(4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)-1 H-pyrrole-2-carboxylate (200 mg, 0.32 mmol) was dissolved in THF (8 mL). A 1 N LiOH solution (8 mL) was introduced and resulting mixture was refluxed for 12 hours. After cooling to room temperature, the mixture was neutralized to pH 7 with 5 N HCl. THF was removed at reduced pressure. The residue was partitioned between ethyl acetate (30 mL) and water (30 mL). The organic phase was washed with brine and dried over anhydrous Na2SO4 and concentrated to give the crude desired product as a yellow solid (190 mg, 97%). LC-MS (Method F): m/z=613.4 [M+H]+; 6.19 min. 1H-NMR (500 MHz, CDCl3): δ 7.74 (s, 1H), 7.53 (d, J=6.0, 1H), 7.30-7.37 (m, 9H), 7.23 (s, 1H), 7.16 (d, J=7.5, 6H), 5.79 (d, J=6.0, 1H), 5.41-5.48 (m, 2H), 3.91 (d, J=11.5, 2H), 3.49 (t, J=11.0, 2H), 2.15 (d, J=12.0, 2H), 1.72-1.79 (m, 2H), 1.42 (d, J=7.0, 6H).

Workup

  1. customresulting mixture
  2. temperaturewas refluxed for 12 hours
  3. customTHF was removed at reduced pressure
  4. customThe residue was partitioned between ethyl acetate (30 mL) and water (30 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-278a46b3c4c040d1b6bb465320552d9d
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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