Hydrochloric Acid → HCID 54544852, compound

HRID 2306741Notes

Reaction equation

HRID 2306741 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[O:27][C:28]([C:31]56OCC(C)(C[O:36]5)[CH2:33][O:32]6)=[CH:29][CH:30]=4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH3:33][O:32][C:31]([C:28]1[O:27][C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][N:17]=[C:16]3[NH:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)=[CH:30][CH:29]=1)=[O:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22609777HCID 22609777, compound

Product 1

HCID 54544852HCID 54544852, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Benzyloxy-phenyl)-(6-(5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-furan-2-yl)-quinazolin-4-yl)-amine (0.680 g, 1.30 mmol) was dissolved in THF (10 ml) and 2N aqueous HCl (10 ml) was added. The mixture was stirred at room temperature for 2 hours. The THF was removed in vacuo and the residue diluted with water to preciptate the intermediate (partial hydrolysis) 5-(4-(4-benzyloxy-phenylamino)-quinazolin-6-yl)-furan-2-carboxylic acid (3-methyloxetan-3-yl)-methyl ester which was collected by filtration and washed with water and acetone; δH [2H6]DMSO 12.10 (1H, s), 9.50 (1H, s), 8.87 (1H, s), 8.43 (1H, s), 8.00 (1H, s), 7.66 (2H, d), 7.58 (1H, d), 7.30-7.54 (6H, m), 7.13 (2H, d), 5.16 (2H, s), 4.14 (2H, s), 3.28-3.41 (4H, m), 0.88 (3H, s). This solid was suspended in a mixture of MeOH (15 ml) and NaOH (2N, 15 ml), and the mixture was stirred at room temperature for 2 hours. The reaction was diluted with water to give the title product as a yellow solid, which was collected by filtration (0.375 g, 0.831 mmol, 64%); δH [2H6]DMSO 10.06 (1H, s), 8.91 (1H, s), 8.48 (1H, s), 8.21 (1H, d), 7.80 (1H, d), 7.63 (2H, d), 7.25-7.52 (7H, m), 7.05 (2H, d), 5.10 (2H, s), 3.85 (3H, s); m/z (M+1+) 452.

Workup

  1. customThe THF was removed in vacuo
  2. additionthe residue diluted with water
  3. filtrationwas collected by filtration
  4. washwashed with water and acetone
  5. additionThis solid was suspended in a mixture of MeOH (15 ml) and NaOH (2N, 15 ml)
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. additionThe reaction was diluted with water

Sources & evidence

ORD record
ord-823e79da8df94246b8bc9d4f254b45eb
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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