Hydrochloric Acid → HCID 178478147, compound

HRID 1068898Notes

Reaction equation

HRID 1068898 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.[NH:19]1[C:23]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)=[N:22][N:21]=[N:20]1.[BH3-]C#N.[Na+].Cl>CN1C(=O)N(C)CC1.CO.C(O)(=O)C>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][CH2:28][C:27]4[CH:26]=[CH:25][C:24]([C:23]5[NH:19][N:20]=[N:21][N:22]=5)=[CH:31][CH:30]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehydeHCID 5003444Sodium cyanoborohydride2×HCID 178509242HCID 178509242, compound

Product 1

HCID 178478147HCID 178478147, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 131722711DMEU methanolSolvent

Procedure

Under a nitrogen atmosphere, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1 H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 261 mg (1.5 mmol) of 4-(tetrazol-5-yl)-benzaldehyde and 180 mg of acetic acid are stirred in 39 ml of DMEU/methanol (1:2) at RT for 1 hour. Then 440 mg (7 mmol) of NaCNBH3 are added and the reaction mixture is heated to boiling. After 15 hours a further 440 mg of NaCNBH3 are added and the reaction mixture is again stirred at boiling temperature for 15 hours, then poured into 0.6 liter of a 1 aqueous K2B4O7.4H2O solution and stirred overnight to complete the reaction. The mixture is acidified to pH 3.9 with 2N HCl and the product that precipitates is filtered off and washed with water. Heating in 20 ml of ethanol and filtration yield 4-(3chloro-phenylamino)-3-[4-(tetrazol-5-yl)-benzylamino]-1H-pyrazolo-[3,4-d]pyrimidine; HPLC:tRet(grad20-100/20)=9.8; MS: (M)+=418.

Workup

  1. temperaturethe reaction mixture is heated to boiling
  2. customfor 15 hours
  3. stirringstirred overnight
  4. customthe reaction
  5. customthe product that precipitates
  6. filtrationis filtered off
  7. washwashed with water
  8. temperatureHeating in 20 ml of ethanol
  9. filtrationfiltration

Sources & evidence

ORD record
ord-72f27a91b58543ac9bb0f178d1fe786a
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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