Acetic Acid → HCID 21951882, compound

HRID 2215866Notes

Reaction equation

HRID 2215866 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:29](=[O:30])[C:28]4[C:23](=[CH:24][C:25](N)=[CH:26][CH:27]=4)[NH:22][C:21]3=[O:32])=[CH:16][CH:15]=2)=[O:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(O)(=O)C.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1C=O.C([BH3-])#[N:45].[Na+]>CS(C)=O>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:29](=[O:30])[C:28]4[C:23](=[CH:24][C:25]([C:38]5[S:37][CH:41]=[CH:40][CH:39]=5)=[CH:26][CH:27]=4)[N:22]([NH2:45])[C:21]3=[O:32])=[CH:16][CH:15]=2)=[O:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21951870HCID 21951870, compound

Product 1

HCID 21951882HCID 21951882, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound 5-Chloro-N-[(4-(7-amino-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenylamino)carbonyl]thiophene-2-sulfonamide (40 mg, 0.08 mmol) was dissolved in methyl sulfoxide (0.5 mL). To it was added acetic acid (1.0 mL) and thiophene-2-carbaldehyde (18 mg, 0.16 mmol). The mixture was stirred for 15 minutes at room temperature. To it was then added sodium cyanoborohydride (21 mg, 0.32 mmol). The mixture was stirred for 30 minutes and quenched with water (2 mL). The reaction mixture was then directly subjected to preparative HPLC purification to yield the title compound (26 mg, 55%). ES+ MS showed 588 m/z and ES− MS 586 m/z, the correct mass for the product.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customquenched with water (2 mL)
  3. customThe reaction mixture was then directly subjected to preparative HPLC purification

Sources & evidence

ORD record
ord-20a064598b8f4198b71aadcf62f903e7
Source dataset
uspto-grants-2006_09
Patent number
US07109332B2

Reaction notes

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