Hydrochloric Acid → HCID 9820619, compound

HRID 480138Notes

Reaction equation

HRID 480138 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH:20]5[CH:21]6[CH:15]3[CH:16]3[CH:19]4[CH:18]5[C:17]36[C:22](O)=[O:23])[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[BH4-].[Na+].Cl>CC#N>[OH:23][CH2:22][C:17]12[CH:18]3[CH:19]4[C:14]5([C:7]6[NH:6][C:5]7[C:4](=[O:25])[N:3]([CH2:26][CH2:27][CH3:28])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=7[N:8]=6)[CH:20]3[CH:21]1[CH:15]5[CH:16]24

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 9800112HCID 9800112, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 9820619HCID 9820619, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-cubane-1-carboxylic acid (100 mg, 0.261 mmol) and HATU (1.1 eq, 0.288 mmol, 110 mg) in 6 ml of MeCN was added Hunig's base (1.1 eq, 0.288 mmol, 37 mg), neat via syringe. The resulting heterogeneous mixture was stirred for 3 h and NaBH4 (2.0 eq, 0.522 mmol, 20 mg) was added in one portion. The mixture was stirred for an additional 2 h, cooled with the aid of an ice bath and acidified by the dropwise addition of concentrated HCl. The resulting pale yellow precipitate was collected, dried, and resuspended in MeCN. After stirring overnight the material was collected and dried to afford an off-white powder (50 mg, 52%). MS: 369 (MH+).

Workup

  1. stirringThe mixture was stirred for an additional 2 h
  2. temperaturecooled with the aid of an ice bath
  3. customThe resulting pale yellow precipitate was collected
  4. customdried
  5. stirringAfter stirring overnight the material
  6. customwas collected
  7. customdried

Sources & evidence

ORD record
ord-fb1f150e9f4b463ab64ff9c2f5db34b0
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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