Lithium hydroxide, monohydrate → HCID 86699337, compound

HRID 706663Notes

Reaction equation

HRID 706663 reaction equation
O1CCN(CCOC2C=CN=C(N)C=2)CC1.[O:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][N:29]3[C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][N:34]=[C:28]3[CH:27]=2)[CH2:19][CH2:18]1.O.[OH-].[Li+:42]>C1COCC1.O.C1COCC1>[CH2:38]([O:37][C:35]([C:32]1[N:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][N:20]3[CH2:19][CH2:18][O:17][CH2:22][CH2:21]3)=[CH:27][C:28]2=[N:34][CH:33]=1)=[O:36])[CH3:39].[O:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][N:29]3[C:32]([C:35]([O-:37])=[O:36])=[CH:33][N:34]=[C:28]3[CH:27]=2)[CH2:19][CH2:18]1.[Li+:42]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 86699338HCID 86699338, compound

Product 1

HCID 86699337HCID 86699337, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ethyl 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate 4-(2-morpholinoethoxy)pyridin-2-amine (1.0 g, 3.13 mmol) was dissolved in a 4:1 THF/water mixture (to a 0.5 M concentration). Lithium hydroxide monohydrate (75 mg, 3.13 mmol) was added and the resulting mixture was stirred overnight at ambient temperature, followed by heating at 65° C. for eight hours. An additional 0.1 equivalents of lithium hydroxide monohydrate was added, and heating at 65° C. was continued overnight. The reaction mixture was diluted with THF, filtered, concentrated, and dried under high vacuum to afford the crude product (0.979 g) as a pale yellow, free flowing solid.

Workup

  1. concentrationto a 0.5 M concentration)
  2. temperatureby heating at 65° C. for eight hours
  3. temperatureheating at 65° C.
  4. waitwas continued overnight
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-352d59681f0d4453956f27779124ef6b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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