Water → [2-((R)-Indan-1-ylamino)-quinolin-6-yl]-urea

HRID 1928713Notes

Reaction equation

HRID 1928713 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N-:22]=[C:23]=[O:24].[K+].O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:23]([NH2:22])=[O:24])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11051572Potassio isocyanateHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 57860970[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-urea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(R)—N2-indan-1-yl-quinoline-2,6-diamine (100 mg, 0.36 mmol) and potassium isocyanate (32 mg, 0.40 mmol) were stirred in a 1:1 mixture of water and acetic acid (3 mL) at ambient temperature for 2 h. Then a satured solution of sodium bicarbonate was added, the aqueous phase was extracted with ethyl acetate, the organic phase washed with brine and dried over sodium sulfate. Over night the desired product precipitated and subsequently the crystals were collected and dried under vacuum. [2-((R)-Indan-1-ylamino)-quinolin-6-yl]-urea was obtained as a white solid (44 mg; 38%); MS: m/e=319.3 (M+H+).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. washthe organic phase washed with brine
  3. dry with materialdried over sodium sulfate
  4. customOver night the desired product precipitated
  5. customsubsequently the crystals were collected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3182189c8a6b4bb1a408b32516885c65
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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