Octanoyl chloride → Octanoic acid(7-octanoyl-4-oxo-4,7-dihydro-3h-pyrrolo[2,3-d]pyrimidin-2-yl)-amide

HRID 412741

Reaction equation

HRID 412741 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:22])[C:5]2[C:10](CNC3C=CC(C(O)=O)=CC=3)=[CH:9][NH:8][C:6]=2[N:7]=1.NC1NC(=O)C2C(CNC3C=C[C:38]([CH2:41][C:42]4[CH:47]=[CH:46][C:45](N)=[CH:44][CH:43]=4)=CC=3)=CNC=2N=1.NC1NC(=[O:60])C2C=CNC=2N=1.[C:61](Cl)(=[O:69])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68]>N1C=CC=CC=1>[C:61]([N:8]1[C:6]2[N:7]=[C:2]([NH:1][C:43](=[O:60])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:42][CH2:41][CH3:38])[NH:3][C:4](=[O:22])[C:5]=2[CH:10]=[CH:9]1)(=[O:69])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68]

Participants

6

Reactant 4

HCID 8124Octanoyl chlorideHCID 1354087147-DeazaguanineHCID 1355153914-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid2×HCID 1360508672-Amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 136050865Octanoic acid(7-octanoyl-4-oxo-4,7-dihydro-3h-pyrrolo[2,3-d]pyrimidin-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The syntheses of 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21 and 2-amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 24 are shown in FIG. 22. FIG. 22A details the synthesis of 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21. 2-amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 15 is reacted with octanoyl chloride in pyridine to produce octanoic acid(7-octanoyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 16, which is then treated with ammonia in methanol to produce octanoic acid(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 17. Octanoic acid(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 17 is reacted with (PhCH2)2NH in formaldehyde to produce octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-amide 18. Octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-amide 18 is reacted with 4-amino-methylbenzoate 19 to yield 4-[(2-octanoylamino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid methyl ester 20. Treatment of 4-[(2-octanoylamino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid methyl ester 20 with 5 M KOH in ethanol yields 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21.

Sources & evidence

ORD record
ord-871543eae7f54cf28f2616e55d73153e
Source dataset
uspto-grants-2003_05
Patent number
US06562969B1

Linked notes

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