Hydrochloric Acid → HCID 21755892, compound

HRID 258308Notes

Reaction equation

HRID 258308 reaction equation
[CH:1]([C:3]12[CH2:17][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)=O.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]2[N:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:21][CH2:20]1.Cl.C([BH3-])#N.[Na+]>CO.[Cl-].[Na+].O>[CH:5]1[C:4]2[C:3]3([CH2:1][N:19]4[CH2:20][CH2:21][CH:22]([NH:25][C:26]5[N:27]=[CH:28][CH:29]=[CH:30][N:31]=5)[CH2:23][CH2:24]4)[CH2:17][CH:10]([C:11]4[C:16]3=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 124041419,10-Dihydro-9,10-methanoanthracene-9-carboxaldehydeHCID 19737304N-(Piperidin-4-yl)pyrimidin-2-amine--hydrogen chloride (1/1)

Product 1

HCID 21755892HCID 21755892, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

9-Formyl-9,10-dihydro-9,10-methanoanthracene (0.683 g, 3.1 mmol) was stirred for 1 hour at room temperature in methanol (7.0 mL) with 2-(4-piperidylamino)pyrimidine hydrochloride (1.000 g, 4.7 mmol, prepared as described below) and activated, powdered, 3 angstrom molecular sieves (0.820 g). The pH was initially adjusted to 6.5 with methanolic hydrogen chloride. Sodium cyanoborohydride (0.137 g, 2.2 mmol) was added and the tan suspension stirred for 23 hours. The suspension was poured into strongly basic (NaOH) brine solution (pH>11) and extracted with methylene chloride. The combined extracts were dried (sodium sulfate) and concentrated to give the crude product. Flash chromatography on silica gel using 15% acetone/hexanes provided the title compound as a white solid (0.225 g, 0.6 mmol, 20%). Using a procedure similar to that described in Example 87, the hydrochloride salt was obtained, mp 290° C. (dec); MS(CI): 456 (M+H); NMR (250 MHz, DMSO-d6): 9.87(br m, 1H), 8.38-8.32(m, 2H), 7.64(br m, 1H), 7.37-7.31(m, 4H), 7.03-6.94(m, 4H), 6.70-6.63(m, 1H), 4.46(s, 1H), 4.34-4.32(m, 2H), 4.16(br m, 1H), 3.60-3.34(m, 4H), 2.73(s, 2 H), 2.11-1.88(m, 4H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined extracts were dried (sodium sulfate)
  3. concentrationconcentrated
  4. customto give the crude product

Sources & evidence

ORD record
ord-75d016c4d75f49d58a36f626161e9af4
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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