Hydrochloric Acid → HCID 178433062, compound

HRID 1371225Notes

Reaction equation

HRID 1371225 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1.C[OH:28].Cl>CCOC(C)=O>[OH2:28].[ClH:1].[N:18]1([C:2]2[N:7]=[C:6]([CH3:8])[NH:5][C:4]3=[CH:9][C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:11][C:3]=23)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10328IndolineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433062HCID 178433062, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask was added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (350 mg, 1.44 mmol) and indoline (Aldrich Chemical Company) (350 mg, 2.94 mmol). The flask was purged with N2 and the mixture was heated to 180° C. for 1 h. The reaction was allowed to cool to room temperature and the crude material was purified by silica gel chromatography with 33% EtOAc/hexanes to give 250 mg (53% yield) of an off white solid. The free base (221 mg, 0.677 mmol) was dissolved in hot EtOAc (15 mL)and MeOH (2 mL) and anhydrous ethereal HCl (0.677 mL, of a 1.0 M soln, 0.677 mmol) was added dropwise. The mixture was stirred for 2 h and allowed to cool to room temperature. The resulting solid was filtered and dried under high vacuum to give 239 mg (97% yield) of the title compound as a light yellow solid. Mp: >300° C. 1H NMR (DMSO-d6; 400 MHz): d 2.7 (s, 3), 4.87 (t, 2, J=8.2), 7.0 (s, 1), 7.17 (t, 1, J=7.5), 7.32 (t, 1, J=7.6), 7.58 (m, 3), 8.0 (d, 2, J=6.9), 8.53 (d, 1, J=3.3), 11.7 (br, 1), 14.55 (br, 1). MS m/z: 327.0 (M+1); 325 (M−1). Anal. Calcd for C21H18N4.1.0HCl.1.25H2O: C, 6.5.45; H, 5.62; N, 14.54. Found: C, 65.62;, H, 5.62; N, 14.49.

Workup

  1. customThe flask was purged with N2
  2. temperatureto cool to room temperature
  3. customthe crude material was purified by silica gel chromatography with 33% EtOAc/hexanes
  4. customto give 250 mg (53% yield) of an off white solid
  5. temperatureto cool to room temperature
  6. filtrationThe resulting solid was filtered
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-02212e2746eb469f85dd43fd2c3232c1
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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