Hydrochloric Acid → HCID 44532110, compound

HRID 2085965Notes

Reaction equation

HRID 2085965 reaction equation
[ClH:1].[CH2:2]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19]3[C:20]4[CH:28]=[C:27]([C:29]5[O:33][C:32]([C:34]([OH:36])=O)=[CH:31][CH:30]=5)[N:26]=[CH:25][C:21]=4[N:22]=[CH:23][N:24]=3)=[CH:15][CH:16]=2)[CH:11]=[N:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[CH3:50][S:51]([CH2:54][CH2:55][NH2:56])(=[O:53])=[O:52].C(N(CC)CC)C.Cl>C1COCC1.CO>[ClH:1].[CH3:50][S:51]([CH2:54][CH2:55][NH:56][C:34]([C:32]1[O:33][C:29]([C:27]2[N:26]=[CH:25][C:21]3[N:22]=[CH:23][N:24]=[C:19]([NH:18][C:14]4[CH:13]=[C:12]5[C:17](=[CH:16][CH:15]=4)[N:9]([CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:10]=[CH:11]5)[C:20]=3[CH:28]=2)=[CH:30][CH:31]=1)=[O:36])(=[O:53])=[O:52]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)HCID 69890959HCID 69890959, compound

Product 1

HCID 44532110HCID 44532110, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5-[4-(1-Benzyl-1H-indazol-5-ylamino)-pyrido-[3,4-d]pyrimidin-6-yl]-furan-2-carboxylic acid hydrochloride (0.125 g, 0.25 mmol) and carbonyl diimidazole (0.052 g, 0.33 mmol) were suspended in dry THF (3 ml) under a nitrogen atmosphere and stirred at room temperature for 7 hours. 2-(Methanesulphonyl)ethylamine hydrochloride (0.080 g, 0.50 mmol) and triethylamine (0.15 ml, 0.11 g, 1.08 mmol) were added, together with further THF (2 ml), and the resulting mixture was stirred at room temperature for 18 hours. The mixture was adsorbed onto silica gel and purified by column chromatography, eluting with 2-10% MeOH/DCM. Concentration of the relevant fractions gave a pale yellow solid. This was resuspended in methanol and treated with ethanolic HCl to give the product as an orange solid, which was collected by filtration, washed with methanol, acetone and ether, and dried in vacuo (0.093 g, 0.154 mmol, 61%); δH [2H6]DMSO 12.00 (1H,s), 9.76 (1H,s), 9.19-9.29 (2H,m), 8.75 (1H,s), 8.28 (1H,s), 8.22 (1H,s), 7.78-7.90 (2H,m), 7.23-7.38 (7H,m), 5.71 (2H,s), 3.50-3.90 (2H obscured by water signal), 3.48 (2H,t), 3.07 (3H,s); m/z (M+1+) 568.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 18 hours
  2. custompurified by column chromatography
  3. washeluting with 2-10% MeOH/DCM
  4. customConcentration of the relevant fractions gave a pale yellow solid

Sources & evidence

ORD record
ord-77bacdefb86d4f3285f39e70ff8474ae
Source dataset
uspto-grants-2004_04
Patent number
US06723726B1

Reaction notes

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